Production Method 1

78-27-3

932-66-1

Reaction Conditions

1.1 Catalysts: Glycerol ,  Iron chloride (FeCl3) ;  10 min, rt

Reference

Deep eutectic solvent-catalyzed Meyer-Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

Rios-Lombardia, Nicolas; Cicco, Luciana; Yamamoto, Kota; Hernandez-Fernandez, Jose A.; Moris, Francisco; et al, Chemical Communications (Cambridge, 2020, 56(96), 15165-15168

Production Method 2

931-49-7

932-66-1

Reaction Conditions

1.1 Catalysts: 1,4-Benzenedimethanol, polymer with naphthalene (sulfonated) Solvents: Water ;  8 h, 120 °C

Reference

Hydration of aromatic terminal alkynes catalyzed by sulfonated condensed polynuclear aromatic (S-COPNA) resin in water

Tanemura, Kiyoshi; Suzuki, Tsuneo, Tetrahedron Letters, 2017, 58(10), 955-958

Production Method 3

931-49-7

932-66-1

Reaction Conditions

1.1 Catalysts: Silver triflate ,  [Bis(1,1-dimethylethyl)[5-methoxy-3,4,6-trimethyl-2′,4′,6′-tris(1-methylethyl)[1… Solvents: Methanol ,  Water ;  20 h, 80 °C

Reference

Ligand Effects in the Gold Catalyzed Hydration of Alkynes

Ebule, Rene E.; Malhotra, Deepika; Hammond, Gerald B.; Xu, Bo, Advanced Synthesis & Catalysis, 2016, 358(9), 1478-1481

Production Method 4

931-49-7

932-66-1

Reaction Conditions

1.1 Reagents: Water Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, gallium salt (3:1) Solvents: Acetic acid ;  2 h, 100 °C

Reference

Efficient hydration of alkynes through acid-assisted Bronsted acid catalysis

Liang, Shengzong; Hammond, Gerald B.; Xu, Bo, Chemical Communications (Cambridge, 2015, 51(5), 903-906

Production Method 5

931-49-7

932-66-1

Reaction Conditions

1.1 Reagents: Water Catalysts: Tin tungsten oxide Solvents: Toluene ;  1 h, 100 °C

Reference

Heterogeneously Catalyzed Efficient Hydration of Alkynes to Ketones by Tin-Tungsten Mixed Oxides

Jin, Xiongjie; Oishi, Takamichi; Yamaguchi, Kazuya; Mizuno, Noritaka, Chemistry - A European Journal, 2011, 17(4), 1261-1267

Production Method 6

931-49-7

932-66-1

Reaction Conditions

1.1 Reagents: Formic acid

Reference

Hydration of alkynes in anhydrous medium with formic acid as water donor

Menashe, Naim; Shvo, Youval, Journal of Organic Chemistry, 1993, 58(26), 7434-9

Production Method 7

78-27-3

932-66-1

Reaction Conditions

1.1 Reagents: Acetic acid ,  Dowex 50W Solvents: Water

Reference

Phenol-catalyzed Claisen orthoester rearrangement of allylic alcohols with trimethyl β-(methoxy)orthopropionate

Iqbal, Fazila; Ateeq, Humayun S.; Malik, Abdul; Ali, Zeeshan; Ali, Zulfiqar, Zeitschrift fuer Naturforschung, 1998, 53(10), 1244-1245

Production Method 8

91890-17-4

932-66-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Water Solvents: Diethyl ether

Reference

Synthetic uses of tosylmethyl isocyanide (TosMIC)

Van Leusen, Daan; Van Leusen, Albert M., Organic Reactions (Hoboken, 2001, 57,

Production Method 9

931-49-7

932-66-1

Reaction Conditions

1.1 Catalysts: Aurate(2-), [1,3-bis[2,6-bis(1-methylethyl)-4-sulfophenyl]-1,3-dihydro-2H-imidaz… Solvents: Methanol ,  Water ;  2 h, 100 °C

Reference

A structure/catalytic activity study of gold(I)-NHC complexes, as well as their recyclability and reusability, in the hydration of alkynes in aqueous medium

Fernandez, Gabriela A.; Chopa, Alicia B.; Silbestri, Gustavo F., Catalysis Science & Technology, 2016, 6(6), 1921-1929

Production Method 10

29372-98-3

932-66-1

Reaction Conditions

1.1 Reagents: Alumina

Reference

Aluminum oxide catalyzed isomerization of acylated cycloalkenes

Hudlicky, T.; Srnak, T., Tetrahedron Letters, 1981, 22(35), 3351-4

Production Method 11

1728-25-2

932-66-1

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Ethanol ,  Water

Reference

Rearrangement of 2-cycloalken-1-ones to 1-cycloalkenyl methyl ketones

Helwig, Reinhard; Hanack, Michael, Justus Liebigs Annalen der Chemie, 1977, (4), 614-23

Production Method 12

931-49-7

932-66-1

Reaction Conditions

1.1 Catalysts: Chloro[(isocyano-κC)cyclohexane]gold ,  Potassium tetrakis(pentafluorophenyl)borate Solvents: Methanol ,  Water ;  24 h, rt

Reference

Hydration of alkynes at room temperature catalyzed by gold(I) isocyanide compounds

Xu, Yun; Hu, Xingbang; Shao, Jing; Yang, Guoqiang; Wu, Youting; et al, Green Chemistry, 2015, 17(1), 532-537

Production Method 13

78-27-3

932-66-1

Reaction Conditions

1.1 Catalysts: Rhenium(1+), tricarbonyl[O,O-diphenyl N-[[(diphenylphosphino-κP)methyl]diphenylp… Solvents: 1-Butyl-3-methylimidazolium hexafluorophosphate ;  1.5 h, 130 °C

Reference

Novel rhenium(I) catalysts for the isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds: an unprecedented recyclable catalytic system in ionic liquids

Garcia-Alvarez, Joaquin; Diez, Josefina; Gimeno, Jose; Seifried, Christine M., Chemical Communications (Cambridge, 2011, 47(22), 6470-6472

Production Method 14

931-49-7

932-66-1

Reaction Conditions

1.1 Catalysts: [1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl-κO]methanesulfonamidato-κO]silver ,  [[2′-[Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphino-κP][1,1′-biphenyl]-3-yl]-1-pyrr… Solvents: Methanol ,  Water ;  8 h, 25 °C

Reference

Au(I) complexes as the efficient catalyst for hydration of alkynes at room temperature

Wu, Gongde; Wang, Xiaoli; Zhang, Liming; Jiang, Taineng, Gaodeng Xuexiao Huaxue Xuebao, 2015, 36(12), 2461-2467

Production Method 15

78-27-3

932-66-1

Reaction Conditions

1.1 Catalysts: Carbon monoxide ,  Platinum tetrachloride Solvents: 1,2-Dichloroethane ,  Water

Reference

Hydration of Alkynes by a PtCl4-CO Catalyst

Baidossi, Waeel; Lahav, Michal; Blum, Jochanan, Journal of Organic Chemistry, 1997, 62(3), 669-672

Production Method 16

931-49-7

932-66-1

Reaction Conditions

1.1 Reagents: Water Catalysts: Sulfuric acid ,  (SP-5-14)-[1,2,3,7,8,12,13,17,18,19-Decadehydro-21,22-dihydro-5,10,15-tris(2,3,4… Solvents: Methanol ;  12 h, 80 °C

Reference

Hydration of terminal alkynes catalyzed by cobalt corrole complex

Lai, Jia-Wei; Liu, Zhao-Yang; Chen, Xiao-Yan; Zhang, Hao; Liu, Hai-Yang, Tetrahedron Letters, 2020, 61(43),

Production Method 17

931-49-7

932-66-1

Reaction Conditions

1.1 Solvents: Trifluoroacetic acid ,  Water ;  2.5 h, rt

Reference

TFA-mediated alkyne hydration reaction to synthesize methyl ketones

Chen, Z. W.; Luo, M. T.; Ye, D. N., Asian Journal of Chemistry, 2014, 26(19), 6528-6530

Production Method 18

143771-14-6

932-66-1

Reaction Conditions

1.1 Reagents: Trimethylsilyl iodide Solvents: Chloroform ;  5 h, rt
1.2 Solvents: Methanol ;  0.5 h, rt

Reference

An investigation of the behavior of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

Aversa, Maria C.; Barattucci, Anna; Bonaccorsi, Paola; Giannetto, Placido, Tetrahedron, 2002, 58(51), 10145-10150

Production Method 19

78-27-3

932-66-1

Reaction Conditions

1.1 Reagents: Dowex 50W Solvents: Acetic acid ,  Water

Reference

Facile approach to versatile chiral intermediates for fused cyclopentanoid natural products

Zulfiquar, Fazila; Malik, Abdul, Zeitschrift fuer Naturforschung, 2001, 56(11), 1227-1234

Production Method 20

78-27-3

932-66-1

Reaction Conditions

1.1 Catalysts: Trifluoromethanesulfonic acid Solvents: Nitromethane ;  2 h, 50 °C
1.2 Catalysts: 1H-Imidazolium, 1-methyl-3-[3-[[[(1,1,2,2,3,3,4,4,4-nonafluorobutyl)sulfonyl]ami… Solvents: Toluene ;  1 h, 50 °C

Reference

"Release and catch" effect of perfluoroalkylsulfonylimide-functionalized imidazole/pyridine on Bronsted acids in organic systems

Ma, Zhong-Hua; You, Li; Ren, Xiao-Fei; Wang, Yun; Gu, Yanlong; et al, ChemCatChem, 2016, 8(21), 3394-3401

1-Acetyl-1-cyclohexene Raw materials

• 1-ETHYNYLCYCLOHEXENE
• cyclooct-2-en-1-one
• 1-[1-(Cyclohex-1-en-1-yl)-1-isocyanoethanesulfonyl]-4-methylbenzene
• (1S,2R,4R)-1-[[(R)-[1-(1-Cyclohexen-1-yl)ethenyl]sulfinyl]methyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
• 1-(Cyclohex-2-enyl)ethanone
• 1-ethynylcyclohexan-1-ol

1-Acetyl-1-cyclohexene Preparation Products

• 1-Acetyl-1-cyclohexene (932-66-1)

• 1. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 2. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 3. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 4. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 5. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Research Brief on 1-Acetyl-1-cyclohexene (CAS: 932-66-1): Recent Advances and Applications in Chemical Biology and Pharmaceutical Sciences

1-Acetyl-1-cyclohexene (CAS: 932-66-1) is a versatile chemical intermediate that has garnered significant attention in recent years due to its potential applications in pharmaceutical synthesis, chemical biology, and materials science. This research brief synthesizes the latest findings on this compound, highlighting its synthetic utility, biological relevance, and emerging applications in drug discovery. Recent studies have demonstrated its role as a key building block in the synthesis of complex heterocycles, which are prevalent in many bioactive molecules.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of 1-Acetyl-1-cyclohexene as a precursor for novel kinase inhibitors. The research team developed a concise synthetic route utilizing this compound to access pyrazole-fused cyclohexene derivatives, which showed promising activity against CDK2 and GSK-3β kinases. The molecular docking studies revealed that the acetyl group at position 1 plays a crucial role in forming hydrogen bonds with key amino acid residues in the ATP-binding pocket of these kinases.

In the field of chemical biology, researchers have recently employed 1-Acetyl-1-cyclohexene as a versatile scaffold for developing activity-based probes. A Nature Chemical Biology publication (2024) described its use in creating covalent inhibitors that target cysteine residues in disease-relevant proteins. The α,β-unsaturated ketone moiety of 1-Acetyl-1-cyclohexene was strategically modified to enhance its reactivity and selectivity, enabling the development of highly specific probes for proteomic studies.

From a synthetic chemistry perspective, advances in catalytic asymmetric reactions using 1-Acetyl-1-cyclohexene have been particularly noteworthy. A recent ACS Catalysis paper (2024) reported a novel organocatalytic approach for the enantioselective synthesis of chiral cyclohexene derivatives. This methodology provides access to enantiomerically pure compounds that are valuable for pharmaceutical development, with the acetyl group serving as both a directing group and a handle for further functionalization.

The pharmaceutical potential of 1-Acetyl-1-cyclohexene derivatives continues to expand, with several research groups investigating their use as anti-inflammatory and anticancer agents. A 2024 study in European Journal of Medicinal Chemistry demonstrated that certain structural analogs exhibit potent inhibition of NF-κB signaling, suggesting potential applications in treating inflammatory diseases. Furthermore, structure-activity relationship studies have provided valuable insights into optimizing the pharmacological properties of these compounds.

Looking forward, the unique chemical properties of 1-Acetyl-1-cyclohexene position it as a valuable tool for drug discovery and chemical biology research. Ongoing studies are exploring its use in fragment-based drug design and as a versatile intermediate for diversity-oriented synthesis. The compound's commercial availability (CAS: 932-66-1) and well-established synthetic protocols make it particularly attractive for both academic and industrial research applications in the chemical and pharmaceutical sciences.

• 60525-78-2(2-Cyclohexen-1-one, 3-methyl-2-(3-methyl-3,7-octadienyl)-, (E)- (9CI))
• 2658-92-6(2-Cyclohexen-1-one,2-(3-buten-1-yl)-3-methyl-)
• 67822-39-3(Ethanone, 1-(cyclohexenyl)-)
• 56745-19-8(2-Cyclohexen-1-one, 3-butyl-2-methyl-)
• 93842-53-6(Cyclohexenone, methyl-)
• 61345-63-9(Cyclohexenone, methylpentyl-)
• 1121-18-2(2-Methylcyclohex-2-en-1-one)
• 823785-56-4(2-Cyclohexen-1-one, 2-undecyl-)
• 87588-68-9(2-Cyclohexen-1-one,2-heptyl-)
• 25435-63-6(2-Cyclohexen-1-one,2-pentyl-)