Cas no 864232-34-8 (Licochalcone E)

Licochalcone E structure
Licochalcone E structure
Product Name:Licochalcone E
CAS No:864232-34-8
MF:C21H22O4
MW:338.396986484528
CID:4551582
PubChem ID:46209991
Update Time:2024-10-26

Licochalcone E Chemical and Physical Properties

Names and Identifiers

    • Licochalcone E
    • (E)-3-[4-Hydroxy-2-methoxy-5-[(2R)-3-methylbut-3-en-2-yl]phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
    • (S)-(?)-Licochalcone E
    • BDBM50344622
    • (E)-3-[4-hydroxy-2-methoxy-5-[(2S)-3-methylbut-3-en-2-yl]phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
    • (S,E)-3-(4-Hydroxy-2-methoxy-5-(3-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
    • (2E)-3-[5-[(1S)-1,2-Dimethyl-2-propen-1-yl]-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one (ACI)
    • 2-Propen-1-one, 3-[5-[(1S)-1,2-dimethyl-2-propenyl]-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-, (2E)- (9CI)
    • CS-0032374
    • HY-N4182
    • AKOS040760126
    • MS-25149
    • 864232-34-8
    • DTXSID40904154
    • CHEMBL1779057
    • SCHEMBL26114169
    • DA-54912
    • (E)-3-(4-hydroxy-2-methoxy-5-((2S)-3-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
    • DTXCID501332039
    • Inchi： 1S/C21H22O4/c1-13(2)14(3)18-11-16(21(25-4)12-20(18)24)7-10-19(23)15-5-8-17(22)9-6-15/h5-12,14,22,24H,1H2,2-4H3/b10-7+/t14-/m0/s1
    • InChI Key： SWPKMTGYQGHLJS-RNVIBTMRSA-N
    • SMILES： C(/C1C=C([C@@H](C)C(=C)C)C(O)=CC=1OC)=C\C(C1C=CC(O)=CC=1)=O

Computed Properties

  • Exact Mass: 338.15180918 g/mol
  • Monoisotopic Mass: 338.15180918 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 6
  • Complexity: 490
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 5
  • Topological Polar Surface Area: 66.8
  • Molecular Weight: 338.4

Experimental Properties

  • Color/Form: Powder

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Licochalcone E Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: N,N-Diethylaniline ;  0.5 h, reflux; reflux → rt
Reference
Semisynthesis of licochalcone E and biological evaluation as vasorelaxant agents
Yoon, Goo; et al, Bulletin of the Korean Chemical Society, 2010, 31(4), 1085-1087

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 3

Reaction Conditions
1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
2.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 4

Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
3.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
4.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
1.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
1.3 2 h, -78 °C → rt
2.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
2.2 4 h, -78 °C
3.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
4.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
5.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
6.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
6.2 Solvents: Tetrahydrofuran ;  4 h, rt
7.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
9.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
10.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 6

Reaction Conditions
1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
1.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
3.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
4.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
4.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
4.3 2 h, -78 °C → rt
5.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
5.2 4 h, -78 °C
6.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
7.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
8.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
9.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
9.2 Solvents: Tetrahydrofuran ;  4 h, rt
10.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
11.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
12.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
13.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 7

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -78 °C
1.2 -78 °C → rt; 2 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
2.2 Solvents: Tetrahydrofuran ;  4 h, rt
2.3 Reagents: Ammonium chloride
3.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
3.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
5.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
6.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
6.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
6.3 2 h, -78 °C → rt
7.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
7.2 4 h, -78 °C
8.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
9.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
10.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
11.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
11.2 Solvents: Tetrahydrofuran ;  4 h, rt
12.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
13.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
14.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
15.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 9

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
1.2 Solvents: Tetrahydrofuran ;  4 h, rt
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
4.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
5.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 10

Reaction Conditions
1.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
2.2 Solvents: Tetrahydrofuran ;  4 h, rt
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
5.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
6.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 11

Reaction Conditions
1.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
2.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
3.2 Solvents: Tetrahydrofuran ;  4 h, rt
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
5.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
6.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
7.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 12

Reaction Conditions
1.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
2.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
3.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
4.2 Solvents: Tetrahydrofuran ;  4 h, rt
5.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
7.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
8.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 13

Reaction Conditions
1.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
1.2 4 h, -78 °C
2.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
3.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
4.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
5.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
5.2 Solvents: Tetrahydrofuran ;  4 h, rt
6.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
7.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
8.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
9.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 14

Reaction Conditions
1.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
2.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
2.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
2.3 2 h, -78 °C → rt
3.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
3.2 4 h, -78 °C
4.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
5.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
6.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
7.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
7.2 Solvents: Tetrahydrofuran ;  4 h, rt
8.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
9.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
10.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
11.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 15

Reaction Conditions
1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
2.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
3.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
3.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
3.3 2 h, -78 °C → rt
4.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
4.2 4 h, -78 °C
5.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
6.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
7.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
8.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
8.2 Solvents: Tetrahydrofuran ;  4 h, rt
9.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
10.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
11.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
12.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 16

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
1.2 Solvents: Tetrahydrofuran ;  4 h, rt
1.3 Reagents: Ammonium chloride
2.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
2.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
4.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
5.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
5.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
5.3 2 h, -78 °C → rt
6.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
6.2 4 h, -78 °C
7.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
8.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
9.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
10.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
10.2 Solvents: Tetrahydrofuran ;  4 h, rt
11.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
12.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
13.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
14.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 17

Reaction Conditions
1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  30 min, 0 °C
1.2 Reagents: Ammonium chloride
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -78 °C
2.2 -78 °C → rt; 2 h, rt
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
3.2 Solvents: Tetrahydrofuran ;  4 h, rt
3.3 Reagents: Ammonium chloride
4.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
4.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
5.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
6.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
7.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
7.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
7.3 2 h, -78 °C → rt
8.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
8.2 4 h, -78 °C
9.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
10.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
11.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
12.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
12.2 Solvents: Tetrahydrofuran ;  4 h, rt
13.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
14.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
15.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
16.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 18

Reaction Conditions
1.1 Reagents: Sodium borohydride Solvents: Methanol ;  30 min, 0 °C
2.1 Reagents: Imidazole Solvents: Dimethylformamide ;  30 min, 0 °C
2.2 Reagents: Ammonium chloride
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -78 °C
3.2 -78 °C → rt; 2 h, rt
4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
4.2 Solvents: Tetrahydrofuran ;  4 h, rt
4.3 Reagents: Ammonium chloride
5.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
5.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
7.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
8.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
8.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
8.3 2 h, -78 °C → rt
9.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
9.2 4 h, -78 °C
10.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
11.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
12.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
13.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
13.2 Solvents: Tetrahydrofuran ;  4 h, rt
14.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
15.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
16.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
17.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 19

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  16 h, rt
2.1 Reagents: Sodium borohydride Solvents: Methanol ;  30 min, 0 °C
3.1 Reagents: Imidazole Solvents: Dimethylformamide ;  30 min, 0 °C
3.2 Reagents: Ammonium chloride
4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -78 °C
4.2 -78 °C → rt; 2 h, rt
5.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
5.2 Solvents: Tetrahydrofuran ;  4 h, rt
5.3 Reagents: Ammonium chloride
6.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
6.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
7.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
8.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
9.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
9.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
9.3 2 h, -78 °C → rt
10.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
10.2 4 h, -78 °C
11.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
12.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
13.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
14.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
14.2 Solvents: Tetrahydrofuran ;  4 h, rt
15.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
16.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
17.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
18.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

Production Method 20

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  5 h, rt
2.1 Reagents: Potassium carbonate Solvents: Acetone ;  16 h, rt
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  30 min, 0 °C
4.1 Reagents: Imidazole Solvents: Dimethylformamide ;  30 min, 0 °C
4.2 Reagents: Ammonium chloride
5.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -78 °C
5.2 -78 °C → rt; 2 h, rt
6.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
6.2 Solvents: Tetrahydrofuran ;  4 h, rt
6.3 Reagents: Ammonium chloride
7.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
7.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide ;  2 h, rt
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 3 h, 0 °C
9.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium perchlorate Solvents: tert-Butanol ,  Water ;  0 °C; 0 °C → rt; 30 min, rt
10.1 Reagents: Triethylamine ,  Pivaloyl chloride Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C; 1 h, 0 °C
10.2 Reagents: Butyllithium ;  -78 °C; 40 min, -78 °C
10.3 2 h, -78 °C → rt
11.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  1.2 h, -78 °C
11.2 4 h, -78 °C
12.1 Reagents: Lithium hydroxide ,  Hydrogen peroxide Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; 4 h, rt
13.1 Reagents: Triethylamine ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 h, rt
14.1 Solvents: Tetrahydrofuran ;  3 h, 0 °C
15.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, rt
15.2 Solvents: Tetrahydrofuran ;  4 h, rt
16.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  3 h, 0 °C
17.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
18.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  48 h, rt
19.1 Reagents: Hydrochloric acid Solvents: Methanol ;  5 h, rt
Reference
An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration
Liu, Zhiguo; et al, Tetrahedron, 2010, 66(17), 3165-3172

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Licochalcone E Preparation Products

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