Clovanediol

Base Information

• Chemical Name: Clovanediol
• CAS No.: 2649-64-1
• Molecular Formula: C15H26 O2
• Molecular Weight: 238.37
• Mol file: 2649-64-1.mol

Synonyms:3a,7-Methano-3aH-cyclopentacyclooctene-3,6-diol,1,2,3a,4,5,6b,7,8,9,9a-decahydro-1,1,7b-trimethyl- (8CI);3a,7-Methano-3aH-cyclopentacyclooctene-3,6-diol, decahydro-1,1,7-trimethyl-,[3S-(3a,3ab,6b,7b,9aa)]-; Clovanediol (6CI,7CI); 2b,9a-Dihydroxyclovane; Clovane-2b,9a-diol; Cloven-2b,9a-diol

Chemical Property of Clovanediol

Chemical Property:

• Melting Point: 159 °C
• Boiling Point: 319.8±10.0 °C(Predicted)
• PKA: 14.90±0.70(Predicted)
• PSA: 40.46000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 2.72470

Purity/Quality:

98%min ^*data from raw suppliers

Clovanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Clovanediol is a natural product found in cloves and other plant species.

Technology Process of Clovanediol

There total 6 articles about Clovanediol 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: 45.0%

caryophyllene oxide (1139-30-6) + phenylmethanethiol (100-53-8) → 4α,11,11-trimethyl-8-methylene-1β,9α-bicyclo[7.2.0]undecan-5-one (68263-68-3) + clovanediol (2649-64-1) + C15H24O + (1S,2S,5S,8R,9R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

Guidance literature:

With zinc(II) chloride; In chloroform; for 5h; Reflux;

DOI:10.1134/S1070428016030076

Reference yield: 29.0%

caryophyllene oxide (1139-30-6) + phenylmethanethiol (100-53-8) → clovanediol (2649-64-1) + (1S,2S,5S,8R,9R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol + (1S,2S,5S,8R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodec-9-ene

Guidance literature:

With zinc(II) chloride; In chloroform; at 20 ℃; for 96h;

DOI:10.1134/S1070428016030076

Reference yield: 9.0%

caryophyllene oxide (1139-30-6) + phenylmethanethiol (100-53-8) → 4α,11,11-trimethyl-8-methylene-1β,9α-bicyclo[7.2.0]undecan-5-one (68263-68-3) + clovanediol (2649-64-1) + C15H24O + (1S,2S,5S,8R,9R)-2-(benzylsulfanyl)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecan-9-ol

Guidance literature:

With zinc(II) chloride; In chloroform; at 20 ℃; for 2h;

DOI:10.1134/S1070428016030076

upstream raw materials:

Caryophyllene oxide

caryophyllene-1β,10α-epoxide

4α,5α-epoxyisocaryophyllene

caryophyllene oxide

Downstream raw materials:

(1S,2S,5S,8R,9R)-2,9-diacetoxyclovane

2β-acetoxyclovan-9α(R)-ol

Refernces

• 1、 Nisnevich, G. A.,Korchagina, D. V.,Makal'skii, V. I.,Dubovenko, Zh. V.,Barkhash, V. A.. "MOLECULAR REARRANGEMENTS OF CARYOPHYLLENE AND ISOCARYOPHYLLENE 4,5-EPOXIDES IN SUPERACIDIC MEDIA". . p. 441 - 453. Retrieved 2007/10/02.