Production Method 1

69498-66-4

818-72-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  2 h, rt

Reference

Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels-Alder/Ene Tandem Reaction

Zheng, Min; et al, Organic Letters, 2016, 18(15), 3554-3557

Production Method 2

1111-64-4

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ,  Hexane ;  1 h, -78 °C
1.2 Reagents: Water Solvents: Tetrahydrofuran ,  Hexane ;  rt

Reference

Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives

Nielsen, Thomas E.; et al, Synthesis, 2004, (9), 1381-1390

Production Method 3

834-16-2

818-72-4

Reaction Conditions

1.1 Reagents: Methanol Catalysts: Trichloroisocyanuric acid ;  6 h, rt

Reference

Efficient tetrahydropyranylation of alcohols and detetrahydropyranylation reactions in the presence of catalytic amount of trichloroisocyanuric acid (TCCA) as a safe, cheap industrial chemical

Firouzabadi, Habib; et al, Synthetic Communications, 2004, 34(19), 3623-3630

Production Method 4

834-16-2

818-72-4

Reaction Conditions

1.1 Catalysts: 1,4-Benzenedicarboxaldehyde, polymer with benzenamine, 4-methylbenzenesulfonate … Solvents: Methanol ;  3 h, rt

Reference

Aniline-terephthalaldehyde resin p-toluenesulfonic acid (ATRT) salt as efficient mild polymeric solid acid catalyst

Tanemura, Kiyoshi; et al, Tetrahedron Letters, 2013, 54(49), 6740-6743

Production Method 5

403857-69-2

818-72-4

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Solvents: Isopropanol

Reference

An Efficient and Highly Selective Deprotecting Method for β-(Trimethylsilyl)ethoxymethyl Ethers

Chen, Ming-Yi; et al, Journal of Organic Chemistry, 2002, 67(4), 1384-1387

Production Method 6

1066-54-2

818-72-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 15 min, -78 °C
1.2 Solvents: Tetrahydrofuran ;  -78 °C; 3 h, -78 °C
1.3 Reagents: Ammonium chloride Solvents: Water
1.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; 15 min, 0 °C
1.5 Reagents: Ammonium chloride Solvents: Water

Reference

Rhodium(I)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage

Guo, Rui; et al, Chemical Science, 2017, 8(4), 3002-3006

Production Method 7

27593-19-7

818-72-4

Reaction Conditions

1.1 Catalysts: Lithium(1+), tris(tetrahydrofuran)-, (T-4)-bis[(1R)-2′-(mercapto-κS)[1,1′-binaph… Solvents: Tetrahydrofuran
1.2 Reagents: Catecholborane
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Enantioselective reduction of prochiral ketones by catecholborane catalyzed by chiral Group 13 complexes

Blake, Alexander J.; et al, Chemistry - A European Journal, 2000, 6(19), 3586-3594

Production Method 8

27593-19-7

818-72-4

Reaction Conditions

Reference

Product subclass 38: trialkylboranes

Zaidlewicz, M.; et al, Science of Synthesis, 2004, 6, 1097-1215

Production Method 9

818-72-4

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Solvents: Methanol

Reference

A novel, highly efficient and selective desilylation method for trialkylsilyl ethers

Lee, Adam Shih-Yuan; et al, Tetrahedron Letters, 1998, 39(29), 5249-5252

Production Method 10

148118-60-9

818-72-4

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Solvents: Methanol

Reference

A novel, highly efficient and selective desilylation method for trialkylsilyl ethers

Lee, Adam Shih-Yuan; et al, Tetrahedron Letters, 1998, 39(29), 5249-5252

Production Method 11

818-72-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Chemo-enzymic synthesis of 13-S-hydroxyoctadecadienoic acid (13-S-HODE)

Chan, Cecil; et al, Biocatalysis, 1990, 3(1-2), 111-18

Production Method 12

818-72-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Chemo-enzymic synthesis of 13-S-hydroxyoctadecadienoic acid (13-S-HODE)

Chan, Cecil; et al, Biocatalysis, 1990, 3(1-2), 111-18

Production Method 13

54315-33-2

818-72-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Chemo-enzymic synthesis of 13-S-hydroxyoctadecadienoic acid (13-S-HODE)

Chan, Cecil; et al, Biocatalysis, 1990, 3(1-2), 111-18

Production Method 14

131928-11-5

818-72-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Chemo-enzymic synthesis of 13-S-hydroxyoctadecadienoic acid (13-S-HODE)

Chan, Cecil; et al, Biocatalysis, 1990, 3(1-2), 111-18

Production Method 15

1111-64-4

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ,  Water

Reference

Preparation of monolithium acetylide in tetrahydrofuran. Reaction with aldehydes and ketones

Midland, M. Mark, Journal of Organic Chemistry, 1975, 40(15), 2250-2

Production Method 16

818-72-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 -
1.3 Reagents: Hydrochloric acid

Reference

Preparation and use of lithium acetylide: 1-methyl-2-ethynyl-endo-3,3-dimethyl-2-norbornanol [preparation]

Midland, M. Mark; et al, Organic Syntheses, 1990, 68, 14-24

Production Method 17

818-72-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane

Reference

Disproportionation of Monolithium Acetylide into Dilithium Carbide and Acetylene Is a Reversible Reaction in Tetrahydrofuran at 0 °C

Mortier, Jacques; et al, Journal of Organic Chemistry, 1998, 63(10), 3515-3516

Production Method 18

818-72-4

Reaction Conditions

1.1 Reagents: Ethylmagnesium bromide Solvents: Tetrahydrofuran ;  45 min, -20 - 10 °C
1.2 < -30 °C; < -30 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C → rt

Reference

Studies on the Cu(I)-Catalyzed Regioselective anti-Carbometalation of Secondary Terminal Propargylic Alcohols

Lu, Zhan; et al, Journal of Organic Chemistry, 2006, 71(7), 2655-2660

Production Method 19

162128-06-5

818-72-4

Reaction Conditions

1.1 Catalysts: Carbon tetrabromide Solvents: Isopropanol

Reference

A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters

Shih-Yuan Lee, A.; et al, Tetrahedron, 2001, 57(11), 2121-2126

Production Method 20

39764-94-8

818-72-4

Reaction Conditions

1.1 Catalysts: Carbon tetrabromide Solvents: Isopropanol

Reference

A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters

Shih-Yuan Lee, A.; et al, Tetrahedron, 2001, 57(11), 2121-2126

Production Method 21

834-16-2

818-72-4

Reaction Conditions

1.1 Catalysts: Carbon tetrabromide Solvents: Methanol

Reference

A simple and efficient hydrolyzing method for tetrahydropyranyl ethers

Lee, Adam Shih-Yuan; et al, Tetrahedron Letters, 1999, 40(7), 1323-1326

Production Method 22

1066-54-2

818-72-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 1 h, -78 °C
1.2 30 min, -78 °C; 30 min, -78 °C → rt
1.3 Reagents: Water ;  rt
1.4 Reagents: Potassium carbonate Solvents: Methanol ;  2 h, rt

Reference

Gold-Catalyzed Ethynylation of Arenes

de Haro, Teresa; et al, Journal of the American Chemical Society, 2010, 132(5), 1512-1513

Production Method 23

4301-14-8

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 3.5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

A general convergent strategy for the synthesis of tetrasubstituted furan fatty acids (FuFAs)

Wang, Yamin; et al, ChemRxiv, 2019, 1, 1-19

Production Method 24

4301-14-8

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C → rt; 3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Diversification of ortho-Fused Cycloocta-2,5-dien-1-one Cores and Eight to Six-Ring Conversion by σ Bond C-C Cleavage

Eccleshare, Lee; et al, Chemistry - A European Journal, 2016, 22(35), 12542-12547

Production Method 25

4301-14-8

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C

Reference

Biosynthesis of the Spiroacetal Suite in Bactrocera tryoni

Booth, Yvonne K.; et al, ChemBioChem, 2011, 12(1), 155-172

Production Method 26

27593-19-7

818-72-4

Reaction Conditions

Reference

Product class 3: propargylic alcohols

Forgione, P.; et al, Science of Synthesis, 2008, 36, 531-571

Production Method 27

60134-93-2

818-72-4

Reaction Conditions

1.1 Catalysts: Nitrosonium tetrafluoroborate Solvents: Methanol ;  4.0 h, rt

Reference

Catalytic removal of tert-butyldimethylsilyl (TBS) and tetrahydropyranyl (THP) groups from protected alcohols by NO+BF4- in methanol

Wang, Jian Tao; et al, Chinese Science Bulletin, 2010, 55(25), 2803-2806

Production Method 28

60134-93-2

818-72-4

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Solvents: Methanol

Reference

A novel, highly efficient and selective desilylation method for trialkylsilyl ethers

Lee, Adam Shih-Yuan; et al, Tetrahedron Letters, 1998, 39(29), 5249-5252

Production Method 29

60134-93-2

818-72-4

Reaction Conditions

1.1 Catalysts: Antimonate(1-), hexachloro-, (OC-6-11)-, salt with 4-bromo-N,N-bis(4-bromophenyl… Solvents: Methanol ;  0.5 - 2.5 h, rt

Reference

A mild and efficient cleavage of tert-butyldimethylsilyl (TBS) and tetrahydropyranyl (THP) ethers using a catalytic amount of TBPA+·SbCl6-

Xu, Yanfen; et al, Tetrahedron Letters, 2008, 49(22), 3634-3637

Production Method 30

178110-05-9

818-72-4

Reaction Conditions

1.1 Solvents: Toluene ,  Tetrahydrofuran

Reference

Sodium Trimethylethynylaluminate, a New Chemoselective Ethynylating Agent

Joung, Meyoung Ju; et al, Journal of Organic Chemistry, 1996, 61(13), 4472-4475

Production Method 31

54655-07-1

818-72-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran
1.2 Reagents: Potassium carbonate Solvents: Methanol

Reference

Facile access to 2,5-disubstituted-4-chloromethyl-3-iodofuran derivatives via ICl-mediated cyclization of 1-alkyl-2-alkynylallylic alcohols

Thongsornkleeb, Charnsak; et al, Tetrahedron Letters, 2012, 53(48), 6615-6619

Production Method 32

818-72-4

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Chemo-enzymic synthesis of 13-S-hydroxyoctadecadienoic acid (13-S-HODE)

Chan, Cecil; et al, Biocatalysis, 1990, 3(1-2), 111-18

1-Octyn-3-ol Raw materials

• 1-Octyn-3-one
• Lithium,[2-(trimethylsilyl)ethynyl]-
• 1-Octyn-3-ol, 1-(trimethylsilyl)-
• 1-Octyn-3-ol, acetate
• 1-OCTYNE, 3-(METHOXYMETHOXY)-
• Silane, [(1-ethynylhexyl)oxy]tris(1-methylethyl)-
• ETHYNYLMAGNESIUM BROMIDE
• 2H-Pyran, 2-[(1-ethynylhexyl)oxy]tetrahydro-
• 1-Octyne, 3-[(2-methoxyethoxy)methoxy]-
• Silane, (1,1-dimethylethyl)[(1-ethynylhexyl)oxy]dimethyl-
• ethynyltrimethylsilane
• Lithium acetylide(Li(C2H)) (9CI)
• Silane, [2-[[(1-ethynylhexyl)oxy]methoxy]ethyl]trimethyl-
• Aluminate(1-), ethynyltrimethyl-, sodium, (T-4)- (9CI)

1-Octyn-3-ol Preparation Products

• 1-Octyn-3-ol (818-72-4)

• 1. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 2. Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes?
  Chandran Rajendran,Govindaswamy Satishkumar,Charlotte Lang,Eric M. Gaigneaux Catal. Sci. Technol., 2020,10, 2583-2592
• 3. An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs)
  R. M. Pemberton,J. P. Hart,T. T. Mottram Analyst, 2001,126, 1866-1871
• 4. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
• 5. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

• 105-31-7(1-Hexyn-3-ol)
• 649561-40-0(1-Tridecyn-3-ol, (3S)-)
• 51703-66-3(1-Heptyn-3-ol, (3S)-)
• 32556-70-0((R)-(+)-1-Octyn-3-ol)
• 32556-71-1((S)-3-Hydroxy-1-octyne)
• 7383-19-9(1-Heptyn-3-ol)
• 649561-36-4(1-Tridecyn-3-ol, (3R)-)
• 649561-34-2(1-Tridecyn-3-ol)
• 65322-71-6(1,9-Decadiyne-3,8-diol)
• 51703-65-2(1-Heptyn-3-ol, (3R)-)