(5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-1-ol

Base Information

• Chemical Name: (5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS No.: 216655-61-7
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID40464647
• Nikkaji Number: J1.803.607J
• Mol file: 216655-61-7.mol

Synonyms:216655-61-7;(5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-1-ol;FT-0671749;DTXSID40464647;(5R)-2-METHYLIDENE-5-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OL

Chemical Property of (5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-1-ol

Chemical Property:

• Boiling Point: 227.4±40.0 °C(Predicted)
• PKA: 14.74±0.40(Predicted)
• PSA: 20.23000
• Density: 0.92±0.1 g/cm3(Predicted)
• LogP: 2.27970
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

97% ^*data from raw suppliers

(5R)-2-Methylene-5-(1-methylethenyl)cyclohexanol(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=C)C(C1)O
• Isomeric SMILES: CC(=C)[C@@H]1CCC(=C)C(C1)O
• Uses: Intermediate in the preparation of Perillaldehyde

Technology Process of (5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-1-ol

There total 8 articles about (5R)-2-Methylidene-5-prop-1-en-2-ylcyclohexan-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: 96.0%

(4R)-limonene 1,2-epoxide (1195-92-2) → (5R)-2-methylene-5-(1-methylethenyl)-1-cyclohexanol (216655-61-7)

Guidance literature:

(4R)-limonene 1,2-epoxide; With diethyl(2,2,6,6-tetramethylpiperidino)aluminium; In hexane; benzene; at 0 - 20 ℃; for 2.75h;

With sodium hydrogencarbonate; In hexane; benzene; at 0 ℃; Saturated solution;

DOI:10.1021/jo101691n

Reference yield: 87.5%

(+)-limonene oxide (1195-92-2,4680-24-4,4959-35-7,6909-30-4,13837-75-7,32543-51-4,42477-94-1,66141-65-9,66141-66-0) → (5R)-2-methylene-5-(1-methylethenyl)-1-cyclohexanol (216655-61-7)

Guidance literature:

With n-butyllithium; N-cyclohexylisopropylamine; methylmagnesium bromide; In diethyl ether; hexane; toluene; at 0 ℃; for 24h;

Reference yield: 26.0%

(4R)-limonene 1,2-epoxide (1195-92-2) → L-carveol (308363-12-4,22567-18-6,20307-86-2) + (5R)-2-methylene-5-(1-methylethenyl)-1-cyclohexanol (216655-61-7) + (1S,2R,4R)-limonene-1,2-epoxide (6909-30-4)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; C₃₀H₃₆CoF₆N₂O₂; triethylamine hydrochloride; zinc; In diethyl ether; at 22 ℃; regioselective reaction; Glovebox;

DOI:10.1021/jacs.9b04993

upstream raw materials:

(+)-limonene oxide

(4R)-limonene 1,2-epoxide

D-limonene

carbon dioxide

Downstream raw materials:

perillyl phenyl sulfoxide

(5R)-2-methylene-5-(1-methylethenyl)-1-cyclohexanone

(+)-acetic acid p-mentha-1,8-dien-7-yl ester

C₁₂H₁₆Cl₃NO