3α-[(R)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-1,2β-dimethylcyclopenta-1β-ol

Base Information

• Chemical Name: 3α-[(R)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-1,2β-dimethylcyclopenta-1β-ol
• CAS No.: 28834-06-2
• Molecular Formula: C₁₅H₂₈O₂
• Molecular Weight: 240.386
• Hs Code.: 2906199090
• Mol file: 28834-06-2.mol

Synonyms:Cyclonerodiol;(1r,2s,3r)-3-[(2r)-2-hydroxy-6-methylhept-5-en-2-yl]-1,2-dimethylcyclopentanol;

Chemical Property of 3α-[(R)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-1,2β-dimethylcyclopenta-1β-ol

Chemical Property:

• Vapor Pressure: 3.25E-06mmHg at 25°C
• Boiling Point: 347.7°Cat760mmHg
• Flash Point: 154°C
• PSA: 40.46000
• Density: 0.971g/cm³
• LogP: 3.28090

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3α-[(R)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-1,2β-dimethylcyclopenta-1β-ol

There total 7 articles about 3α-[(R)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-1,2β-dimethylcyclopenta-1β-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: 33.0%

1-((1R,2S,3R)-3-hydroxy-2,3-dimethylcyclopentyl)ethanone (15356-64-6) + prenyl bromide (870-63-3) → cyclonerodiol (28834-06-2)

Guidance literature:

prenyl bromide; With lithium; In diethyl ether; at 10 - 20 ℃; for 0.833333h;

1-((1R,2S,3R)-3-hydroxy-2,3-dimethylcyclopentyl)ethanone; In tetrahydrofuran; diethyl ether; at 78 ℃; for 5h;

DOI:10.1039/c4ob02021a

Reference yield:

(3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol (443361-64-6) → cyclonerodiol (28834-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bis(cyclopentadienyl)titanium dichloride; manganese; triethylamine / tetrahydrofuran / 0.33 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C

2.2: 0.25 h

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C / Inert atmosphere; Reflux

4.1: potassium osmate(VI) dihydrate; sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / -78 °C

5.1: lithium / diethyl ether / 0.83 h / 10 - 20 °C

5.2: 5 h / 78 °C

With bis(cyclopentadienyl)titanium dichloride; potassium osmate(VI) dihydrate; manganese; sodium periodate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; water; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1039/c4ob02021a

Reference yield:

(1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol (1280572-66-8) → cyclonerodiol (28834-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C

1.2: 0.25 h

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C / Inert atmosphere; Reflux

3.1: potassium osmate(VI) dihydrate; sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / -78 °C

4.1: lithium / diethyl ether / 0.83 h / 10 - 20 °C

4.2: 5 h / 78 °C

With potassium osmate(VI) dihydrate; sodium periodate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium; sodium hydride; In tetrahydrofuran; diethyl ether; water; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1039/c4ob02021a

upstream raw materials:

(3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol

1-((1R,2S,3R)-3-hydroxy-2,3-dimethylcyclopentyl)ethanone

prenyl bromide

(1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol