1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI)

Base Information

• Chemical Name: 1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI)
• CAS No.: 664987-43-3
• Molecular Formula: C9H16O2
• Molecular Weight: 156.22
• Mol file: 664987-43-3.mol

Synonyms:1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI)

Chemical Property of 1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI)

Chemical Property:

• PSA: 40.46000
• LogP: 1.22850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI)

There total 7 articles about 1,3-Cyclooctanediol, 2-methylene-, (1R,3S)-rel- (9CI) 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: 70.0%

cis-2-(tert-butyldimethylsilyloxy)-8-hydroxy-1-methylenecyclooctane → cis-2,8-dihydroxy-1-methylenecyclooctane (664987-43-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo0358675

Reference yield:

(5Z)-2-hydroxycycloocten-1-one (56879-17-5) → cis-2,8-dihydroxy-1-methylenecyclooctane (664987-43-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / hydrogen / palladium on carbon / ethanol / 3.17 h / 760 Torr

2.1: 86 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / Heating

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: chlorotrimethylsilane / tetrahydrofuran / -78 - 20 °C

3.3: 60 percent / m-chloroperbenzoic acid

4.1: 42 percent / titanium tetrachloride / tetrahydrofuran / 24 h / 20 °C

5.1: 94 percent / IBX / tetrahydrofuran; dimethylsulfoxide / 12 h / 20 °C

6.1: 93 percent / sodium borohydride; cerium trichloride heptahydrate / methanol / 0 - 20 °C

7.1: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 6.1: Luche reduction;

DOI:10.1021/jo0358675

Reference yield:

2-hydroxycylooctanone (496-82-2) → cis-2,8-dihydroxy-1-methylenecyclooctane (664987-43-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / Heating

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

2.2: chlorotrimethylsilane / tetrahydrofuran / -78 - 20 °C

2.3: 60 percent / m-chloroperbenzoic acid

3.1: 42 percent / titanium tetrachloride / tetrahydrofuran / 24 h / 20 °C

4.1: 94 percent / IBX / tetrahydrofuran; dimethylsulfoxide / 12 h / 20 °C

5.1: 93 percent / sodium borohydride; cerium trichloride heptahydrate / methanol / 0 - 20 °C

6.1: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; titanium tetrachloride; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 5.1: Luche reduction;

DOI:10.1021/jo0358675

upstream raw materials:

2-hydroxycylooctanone

(5Z)-2-hydroxycycloocten-1-one

2-(tert-butyldimethylsiloxy)cyclooctanone

3-(tert-butyldimethylsilyloxy)-2-methylenecyclooctanone

Downstream raw materials:

(2S,8R)-2,8-dihydroxycyclooctanone