Cembra-2,7,11-triene-4,6-diol

Base Information

Chemical Name:Cembra-2,7,11-triene-4,6-diol
CAS No.:57605-80-8
Molecular Formula:C20H34 O2
Molecular Weight:306.489
Hs Code.:
ChEMBL ID:CHEMBL404253
Metabolomics Workbench ID:52763
NSC Number:751726
Wikidata:Q27105164
Mol file:57605-80-8.mol

Synonyms:4R-cembranoid;cembra-2,7,11-triene-4,6-diol

Suppliers and Price of Cembra-2,7,11-triene-4,6-diol

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

TRC
α-Cembrenediol
25mg
$ 465.00

Total 7 raw suppliers

Chemical Property of Cembra-2,7,11-triene-4,6-diol

Chemical Property:

Vapor Pressure:2.87E-09mmHg at 25°C
Boiling Point:431.8°Cat760mmHg
PKA:14.13±0.70(Predicted)
Flash Point:187.4°C
PSA：40.46000
Density:0.932g/cm³
LogP:4.78340
Storage Temp.:-20°C Freezer
Solubility.:Chloroform (Slightly), Methanol (Slightly)
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:306.255880323
Heavy Atom Count:22
Complexity:431

Purity/Quality:

99% ^*data from raw suppliers

α-Cembrenediol ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1=CCCC(=CC(CC(C=CC(CC1)C(C)C)(C)O)O)C
Isomeric SMILES:C/C/1=C\CC/C(=C/[C@@H](C[C@](/C=C/[C@@H](CC1)C(C)C)(C)O)O)/C
Uses α-Cembrenediol is an antitumor agent found in cigarette smoke condensate.

Technology Process of Cembra-2,7,11-triene-4,6-diol

There total 31 articles about Cembra-2,7,11-triene-4,6-diol 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: 75.0%

: 123311-95-5
(1S,2R,3S,4S,6R)-(7E,11E)-1-Isopropyl-2-<(methylsulfonyl)oxy>-3,4-epoxy-4,8,12-trimethyl-7,11-cyclotetradecadien-6-ol

: 57605-80-8
(4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol

Guidance literature:: With ammonia; sodium; In tetrahydrofuran; at -40 ℃;
DOI:10.1021/jo00288a038

Reference yield:

: 104465-86-3
(2E,6E,10E)-3,7,11-trimethyl-12-<(tert-butyldimethylsilyl)oxy>-2,6,10-dodecatrien-1-ol

: 57605-80-8
(4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol

Guidance literature:: Multi-step reaction with 18 steps

1: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

2: 96 percent / diethyl ether; toluene / 6 h / -20 °C

3: 96 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

4: 98 percent / 1.1M n-Bu₄NF / tetrahydrofuran / 5 h / 0 °C

5: 84 percent / LiCl, methanesulfonyl chloride, 2,6-lutidine / dimethylformamide / 2.5 h / 0 °C

6: 83 percent / 1.)n-BuLi, 1,10-phenanthroline / tetrahydrofuran / 1.)-78 deg C, 1 h, 2.)0 deg C, 0.5 h

7: 1.)EtMgBr, 1,10-phenanthroline / 1.)THF, HMPA, 0 deg C, 5 min., 2.)reflux, 4 h

8: 85 percent / pyridinium p-toluenesulfonate / methanol / 16 h / Ambient temperature

9: 80 percent / triethylamine, DMAP / CH₂Cl₂ / Ambient temperature

10: 90 percent / n-BuLi / pentane; tetrahydrofuran / 3 h / -78 °C

11: 96 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -78 °C

12: 86 percent / CuI / tetrahydrofuran / 0 °C

13: 96 percent / 0.1M DIBAH / tetrahydrofuran; hexane / 1 h / -78 °C

14: 69 percent / H₂ / (Ph₃P)3RhCl / ethanol; benzene / 4 h

15: 88 percent / 3.9 M t-BuOOH / VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 1 h / Ambient temperature

16: 92 percent / CH₂Cl₂; pyridine / 18 h / 0 °C

17: 92 percent / 1.1M Bu₄NF / tetrahydrofuran / 2 h / 0 °C

18: 75 percent / Na, NH₃-gas / tetrahydrofuran / -40 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; copper(l) iodide; n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium chloride; Wilkinson's catalyst; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene;
DOI:10.1021/jo00288a038

Reference yield:

: 121747-11-3
(2E,6E,10E)-12-<(tert-Butyldimethylsilyl)oxy>-3,7,11-trimethyl-2,6,10-dodecatrienal

: 57605-80-8
(4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol

Guidance literature:: Multi-step reaction with 17 steps

1: 96 percent / diethyl ether; toluene / 6 h / -20 °C

2: 96 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

3: 98 percent / 1.1M n-Bu₄NF / tetrahydrofuran / 5 h / 0 °C

4: 84 percent / LiCl, methanesulfonyl chloride, 2,6-lutidine / dimethylformamide / 2.5 h / 0 °C

5: 83 percent / 1.)n-BuLi, 1,10-phenanthroline / tetrahydrofuran / 1.)-78 deg C, 1 h, 2.)0 deg C, 0.5 h

6: 1.)EtMgBr, 1,10-phenanthroline / 1.)THF, HMPA, 0 deg C, 5 min., 2.)reflux, 4 h

7: 85 percent / pyridinium p-toluenesulfonate / methanol / 16 h / Ambient temperature

8: 80 percent / triethylamine, DMAP / CH₂Cl₂ / Ambient temperature

9: 90 percent / n-BuLi / pentane; tetrahydrofuran / 3 h / -78 °C

10: 96 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -78 °C

11: 86 percent / CuI / tetrahydrofuran / 0 °C

12: 96 percent / 0.1M DIBAH / tetrahydrofuran; hexane / 1 h / -78 °C

13: 69 percent / H₂ / (Ph₃P)3RhCl / ethanol; benzene / 4 h

14: 88 percent / 3.9 M t-BuOOH / VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 1 h / Ambient temperature

15: 92 percent / CH₂Cl₂; pyridine / 18 h / 0 °C

16: 92 percent / 1.1M Bu₄NF / tetrahydrofuran / 2 h / 0 °C

17: 75 percent / Na, NH₃-gas / tetrahydrofuran / -40 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; copper(l) iodide; n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium chloride; Wilkinson's catalyst; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene;
DOI:10.1021/jo00288a038