(1S,2Z)-1-Cyclohexyl-2-butene-1-ol

Base Information

• Chemical Name: (1S,2Z)-1-Cyclohexyl-2-butene-1-ol
• CAS No.: 130930-52-8
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• DSSTox Substance ID: DTXSID001256222
• Nikkaji Number: J2.349.961D
• Mol file: 130930-52-8.mol

Synonyms:SCHEMBL14262337;DTXSID001256222;(1S,2Z)-1-Cyclohexyl-2-butene-1-ol;(alphaS)-alpha-(1Z)-1-Propen-1-ylcyclohexanemethanol;130930-52-8

Chemical Property of (1S,2Z)-1-Cyclohexyl-2-butene-1-ol

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 123

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CC(C1CCCCC1)O
• Isomeric SMILES: C/C=C\[C@H](C1CCCCC1)O

Technology Process of (1S,2Z)-1-Cyclohexyl-2-butene-1-ol

There total 26 articles about (1S,2Z)-1-Cyclohexyl-2-butene-1-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: 100.0%

(S)-1-cyclohexylbut-2-yn-1-ol → (Z,S)-α-(1-Propenyl)cyclohexanemethanol (130930-52-8)

Guidance literature:

With hydrogen; In cyclohexane; under 2689.24 Torr;

DOI:10.24820/ark.5550190.p010.902

Reference yield: 84.0%

trans-2-propenyl bromide (590-15-8) + cyclohexanecarbaldehyde (2043-61-0) → (2E,1S)-1-cyclohexyl-2-buten-1-ol (18736-82-8,79605-62-2,79646-42-7,120849-47-0,130930-52-8,137764-95-5,106499-63-2)

Guidance literature:

trans-2-propenyl bromide; With lithium; In diethyl ether; at -35 ℃; for 2h; Inert atmosphere;

With zinc dibromide; In diethyl ether; at -35 - 0 ℃; Inert atmosphere;

cyclohexanecarbaldehyde; optical yield given as %ee; Further stages;

DOI:10.1021/ol702989g

Reference yield: 82.0%

(Z)-1-propenyl bromide (590-13-6) + lithium N-methylephedrate (132350-99-3) + cyclohexanecarbaldehyde (2043-61-0) → (Z,S)-α-(1-Propenyl)cyclohexanemethanol (130930-52-8)

Guidance literature:

(Z)-1-propenyl bromide; With lithium; In diethyl ether; at -35 ℃; for 2h;

With zinc dibromide; In diethyl ether; at 0 ℃; for 1h;

lithium N-methylephedrate; cyclohexanecarbaldehyde; more than 3 stages;

upstream raw materials:

trans-Crotonaldehyde

cyclohexylmagnesium bromide

cyclohexyl chloride

α-cyclohexyl-3-methyloxiranemethanol

Downstream raw materials:

(2E,1R)-1-cyclohexyl-2-buten-1-ol

(2E,1S)-1-cyclohexyl-2-buten-1-ol

(S)-Cyclohexyl-((2S,3S)-3-methyl-oxiranyl)-methanol

(S)-Cyclohexyl-((2R,3R)-3-methyl-oxiranyl)-methanol