3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-

Base Information

• Chemical Name: 3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-
• CAS No.: 915301-61-0
• Molecular Formula: C15H26O2
• Molecular Weight: 238.37
• DSSTox Substance ID: DTXSID50475385
• Nikkaji Number: J2.412.083J
• Mol file: 915301-61-0.mol

Synonyms:915301-61-0;3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-;5-[(1R)-1,5-Dimethyl-4-hexen-1-yl]-2-methyl-3-cyclohexene-1,1-diol;2-METHYL-5-[(2R)-6-METHYLHEPT-5-EN-2-YL]CYCLOHEX-3-ENE-1,2-DIOL;CTK3G4317;DTXSID50475385;AKOS030240920

Chemical Property of 3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 238.193280068
• Heavy Atom Count: 17
• Complexity: 302

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1CC(C(C=C1)(C)O)O
• Isomeric SMILES: C[C@H](CCC=C(C)C)C1CC(C(C=C1)(C)O)O

Technology Process of 3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-

There total 5 articles about 3-Cyclohexene-1,2-diol, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-2-methyl- 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: 95.0%

6-hydroxy-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone (915235-16-4) + methyl iodide (74-88-4) → 2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol (915301-61-0)

Guidance literature:

methyl iodide; With magnesium; In diethyl ether; at 20 ℃; for 2h;

6-hydroxy-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone; In diethyl ether; at 20 ℃; for 12h;

DOI:10.1021/jo061730d

Reference yield: 95.0%

6-hydroxy-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone (915235-16-4) + methyl magnesium iodide (917-64-6) → 2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol (915301-61-0)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2006.11.135

Reference yield:

4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one (196193-23-4) → 2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol (915301-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA; TMSCl / tetrahydrofuran / -78 - 20 °C

1.2: m-CPBA; NaHCO₃ / H₂O; CH₂Cl₂ / 5 h / 0 - 20 °C

1.3: 70 percent / HCl / CH₂Cl₂

2.1: 95 percent / tetrahydrofuran / 0 - 20 °C

With chloro-trimethyl-silane; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2006.11.135

upstream raw materials:

6-hydroxy-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone

methyl iodide

methyl magnesium iodide

4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one

Downstream raw materials:

2-hydroxy-2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-enyl acetate

5-(1,5-dimethyl-hex-4-enyl)-2-hydroxy-2-methyl-cyclohex-3-enone

(R)-(-)-xanthorrhizol

6-(3-methoxy-4-methyl-phenyl)-2-methyl-hept-2-enoyl chloride