Cubebol

Base Information

Chemical Name:Cubebol
CAS No.:23445-02-5
Molecular Formula:C15H26 O
Molecular Weight:222.371
Hs Code.:
UNII:9C9ZTS2B3U
DSSTox Substance ID:DTXSID90177997
Metabolomics Workbench ID:168043
Nikkaji Number:J16.596D
Wikidata:Q726875
Wikipedia:Cubebol
Mol file:23445-02-5.mol

Synonyms:cubebol

Suppliers and Price of Cubebol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 16 raw suppliers

Chemical Property of Cubebol

Chemical Property:

PSA：20.23000
LogP:3.46570
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:222.198365449
Heavy Atom Count:16
Complexity:311

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1CCC(C2C13C2C(CC3)(C)O)C(C)C
Isomeric SMILES:C[C@@H]1CC[C@H]([C@H]2[C@]13[C@@H]2[C@@](CC3)(C)O)C(C)C

Technology Process of Cubebol

There total 22 articles about Cubebol 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%

: 917-54-4
methyllithium

: 890524-61-5
(-)-(1R,5R,6R,7S,10R)-7-isopropyl-10-methyl-tricyclo[4.4.0.0^1,5]decane-4-one

: 23445-02-5
(-)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0^1,5]decane-4-ol

Guidance literature:: methyllithium; With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

(-)-(1R,5R,6R,7S,10R)-7-isopropyl-10-methyl-tricyclo[4.4.0.0^1,5]decane-4-one; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 0.75h; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/chem.200901292

Reference yield: 30.0%

: 372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5
farnesyl pyrophosphate

: 23445-02-5
(-)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0^1,5]decane-4-ol

Guidance literature:: With DL-dithiothreitol; cubebol synthase from Coprinus cinereus; pyrophosphatase from S_. cerevisiae; magnesium chloride; In aq. buffer; at 30 ℃; for 15h; pH=8; Enzymatic reaction;
DOI:10.1002/anie.201805526

Reference yield:

: (1R,4S,4aR,8aR)-8a-hydroxy-4-isopropyl-1-methyl-7-oxodecahydronaphthalene-4a-carbonitrile

: 23445-02-5
(-)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0^1,5]decane-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18.25 h / 0 - 20 °C

2: triethylamine / tetrahydrofuran / 1 h / 0 °C

3: palladium diacetate / acetonitrile / 1.5 h / 20 °C

4: acetonitrile / 3 h / 20 °C / UV-irradiation; Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 0.5 h / 20 °C

6: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 20 °C

7: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium; tert-butyl alcohol / diethyl ether / 16 h / 0 - 20 °C

8: pyridinium p-toluenesulfonate / acetone / 1.5 h / 20 °C

9: cerium(III) chloride / tetrahydrofuran / 16 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; cerium(III) chloride; palladium 10% on activated carbon; hydrogen; palladium diacetate; potassium; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; trifluoroacetic anhydride; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/acs.orglett.6b03635