Cyclohexanol, 2-ethynyl-, (1R,2R)-rel-

Base Information

• Chemical Name: Cyclohexanol, 2-ethynyl-, (1R,2R)-rel-
• CAS No.: 61967-61-1
• Molecular Formula: C8H12O
• Molecular Weight: 124.183
• DSSTox Substance ID: DTXSID201300398
• Nikkaji Number: J682.591E
• Mol file: 61967-61-1.mol

Synonyms:Cyclohexanol, 2-ethynyl-, (1R,2R)-rel-;61967-61-1;DTXSID201300398;rel-(1R,2R)-2-Ethynylcyclohexanol

Chemical Property of Cyclohexanol, 2-ethynyl-, (1R,2R)-rel-

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 124.088815002
• Heavy Atom Count: 9
• Complexity: 131

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1CCCCC1O
• Isomeric SMILES: C#C[C@@H]1CCCC[C@@H]1O

Technology Process of Cyclohexanol, 2-ethynyl-, (1R,2R)-rel-

There total 18 articles about Cyclohexanol, 2-ethynyl-, (1R,2R)-rel- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

C15H14ClNO4 → (1S*, 2S*)-2-ethynylcyclohexanol (61967-61-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

Reference yield: 69.0%

2-ethynylcyclohexanone (62958-02-5) → (1S*, 2S*)-2-ethynylcyclohexanol (61967-61-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1021/ja00415a020

Reference yield: 40.0%

vinyl acetate (108-05-4,9003-20-7) + (1S*, 2S*)-2-ethynylcyclohexanol (61967-61-1) → (1R,2R)-2-ethynylcyclohexanol (5877-41-8,55506-28-0,61967-61-1,69647-64-9,134108-74-0) + (1S,2S)-2-Ethynyl-cyclohexanol + Acetic acid (1R,2R)-2-ethynyl-cyclohexyl ester

Guidance literature:

With 4 A molecular sieve; Lipase PS (Amano); In toluene; at 30 ℃; for 6h;

DOI:10.1016/S0040-4039(03)01514-4

upstream raw materials:

vinyl acetate

Succinimide

trans-2-ethynylcyclohexan-1-ol

2-ethynylcyclohexanone

Downstream raw materials:

(1R,2R)-2-ethynylcyclohexanol

cis-1-(3,5-dinitrobenzoyloxy)-2-ethynylcyclohexane

Refernces

• 1、 Ye, Longwu,Cui, Li,Zhang, Guozhu,Zhang, Liming. "Alkynes as equivalents of α-diazo ketones in generating α-oxo metal carbenes: A gold-catalyzed expedient synthesis of dihydrofuran-3-ones". supporting information; experimental part. p. 3258 - 3259. Retrieved 2010/05/01.
• 2、 Sukeda, Makoto,Ichikawa, Satoshi,Matsuda, Akira,Shuto, Satoshi. "The first radical method for the introduction of an ethynyl group using a silicon tether and its application to the synthesis of 2′-deoxy-2′-C-ethynylnucleosides". . p. 3465 - 3475. Retrieved 2007/10/03.