(1S,3R,4Z,8Z,12S,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-diol

Base Information

• Chemical Name: (1S,3R,4Z,8Z,12S,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-diol
• CAS No.: 57605-80-8
• Molecular Formula: C20H34 O2
• Molecular Weight: 306.489
• Nikkaji Number: J148.814G,J1.483.448F
• Wikidata: Q105237187
• Mol file: 57605-80-8.mol

Synonyms:2,7,11-cembratriene-4,6-diol;2,7,11-cembratriene-4,6-diol, beta-isomer

Chemical Property of (1S,3R,4Z,8Z,12S,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-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:

98% ^*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 (1S,3R,4Z,8Z,12S,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-diol

There total 31 articles about (1S,3R,4Z,8Z,12S,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-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%

(1S,2R,3S,4S,6R)-(7E,11E)-1-Isopropyl-2-<(methylsulfonyl)oxy>-3,4-epoxy-4,8,12-trimethyl-7,11-cyclotetradecadien-6-ol (123311-95-5) → (4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol (57605-80-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -40 ℃;

DOI:10.1021/jo00288a038

Reference yield:

(2E,6E,10E)-3,7,11-trimethyl-12-<(tert-butyldimethylsilyl)oxy>-2,6,10-dodecatrien-1-ol (104465-86-3) → (4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol (57605-80-8)

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:

(2E,6E,10E)-12-<(tert-Butyldimethylsilyl)oxy>-3,7,11-trimethyl-2,6,10-dodecatrienal (121747-11-3) → (4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol (57605-80-8)

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

upstream raw materials:

(1S,2E,4R,6R,7E,11E)-cembra-2,7,11-triene-4,6-diol

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

(1S,2E,4R,6E,8S,11E)-2,6,11-cembratriene-4,8-diol

(1S,2E,4S,6E,8S,11E)-2,6,11-cembratriene-4,8-diol

Refernces

• 1、 Marshall,Robinson,Lebreton. "Synthesis of the tumor inhibitory tobacco constituents α- and β-2,7,11-cembratriene-4,6-diol by diastereoselective [2,3] wittig ring contraction". . p. 227 - 239. Retrieved 2007/10/02.
• 2、 Begley, Michael J.,Crombie, Leslie,McNamara, Desmond,Firth, David F.,Smith, Sue,Bevan, Peter C.. "Cembrenediols in the curing of tobacco. X-ray crystal structures of β-cembrenediol and α-cembreneketol". . p. 1695 - 1703. Retrieved 2007/10/02.