4-Cyclohexyl-3-butyn-2-ol

Base Information

• Chemical Name: 4-Cyclohexyl-3-butyn-2-ol
• CAS No.: 65199-70-4
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID701312352
• Mol file: 65199-70-4.mol

Synonyms:4-Cyclohexyl-3-butyn-2-ol;SCHEMBL12341326;DTXSID701312352;65199-70-4

Chemical Property of 4-Cyclohexyl-3-butyn-2-ol

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 166

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C#CC1CCCCC1)O

Technology Process of 4-Cyclohexyl-3-butyn-2-ol

There total 6 articles about 4-Cyclohexyl-3-butyn-2-ol 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: 94.0%

1,1-dibromo-2-cyclohexylethene (60754-49-6) + acetaldehyde (75-07-0,9002-91-9) → (+/-)-4-cyclohexyl-but-3-yn-2-ol (65199-70-4)

Guidance literature:

1,1-dibromo-2-cyclohexylethene; With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2.5h;

acetaldehyde; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

DOI:10.1016/j.tet.2005.08.063

Reference yield: 86.0%

2-cyclohexylacetylene (931-48-6) + acetaldehyde (75-07-0,9002-91-9) → (+/-)-4-cyclohexyl-but-3-yn-2-ol (65199-70-4)

Guidance literature:

2-cyclohexylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

acetaldehyde; at -78 - 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/chem.201403293

Reference yield:

cyclohexanecarbaldehyde (2043-61-0) → (+/-)-4-cyclohexyl-but-3-yn-2-ol (65199-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 74 percent / CH₂Cl₂ / 12 h / 20 °C

2.1: methyllithium / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

2.2: 94 percent / diethyl ether; tetrahydrofuran / -78 - 20 °C

With methyllithium; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja0521831

upstream raw materials:

2-cyclohexylacetylene

ethylmagnesium bromide

fluoroethyne

cyclohexylmagnesiumchloride

Downstream raw materials:

(S)-4-cyclohexyl-but-3-yn-2-ol

3-cyclohexyl-1-methylprop-2-ynyl acetate

(3-bromobut-1-yn-1-yl)cyclohexane