(+)-Epicubenol

Base Information

• Chemical Name: (+)-Epicubenol
• CAS No.: 19912-67-5
• Molecular Formula: C15H26O
• Molecular Weight: 222.37
• Mol file: 19912-67-5.mol

Synonyms:

Chemical Property of (+)-Epicubenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Epicubenol

There total 22 articles about (+)-Epicubenol 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: 1.0%

4-epi-cubebil (38230-60-3) → cubenol (19912-67-5,21284-22-0,38757-58-3,68199-14-4,73365-77-2,81939-29-9) + 1–epi–cubenol (19912-67-5) + delta-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + (1R,10R)-zonarene (41929-05-9)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.54.2366

Reference yield: 1.0%

4-epi-cubebil (38230-60-3) → cubenol (19912-67-5,21284-22-0,38757-58-3,68199-14-4,73365-77-2,81939-29-9) + 1–epi–cubenol (19912-67-5) + delta-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + (1R,10R)-zonarene (41929-05-9)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.54.2366

Reference yield:

4-isopropyl-7-methyl-octa-5t,7-dienal (60796-18-1) → (+/-)-epicubenol (19912-67-5,21284-22-0,38757-58-3,68199-14-4,73365-77-2,81939-29-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / tetrahydrofuran / 1 h / Ambient temperature

2: periodinane / CH₂Cl₂

3: benzene / 2 h / 120 °C / sealed tube

4: 15 percent / (Ph₃P)3RhCl / 0.08 h / 93 °C

5: 1.) LHMDS; 2.) Et₃N / 1.) THF, -78 deg C, 15 min; RT, 16 h; 2.) THF, RT, 10 min

6: 1.) m-CPBA; 2.) aq 1N HCl / 1.) CH₂Cl₂, RT, 1 h; 2.) acetonitrile

7: 78 percent / NaH / dimethylsulfoxide / 5 h / Ambient temperature

8: NaBH₄, CoCl₂*6H₂O / ethanol / 14 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; cobalt(II) chloride; lithium hexamethyldisilazane; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4039(00)73497-6

upstream raw materials:

4-epi-cubebil

(1R,2R,4aR,5R,8S,8aR)-8-Isopropyl-2,5-dimethyl-4a-trimethylsilanyloxy-decahydro-naphthalen-1-ol

(-)-<2R-(2α,4aα,5α,8β,8aβ)>-octahydro-4a-hydroxy-2,5-dimethyl-8-(1-methylethyl)-1(2H)-naphthalenone

(+)-bicyclogermacrane-1,8-dione

Refernces

• 1、 Gijsen, Harrie J. M.,Wijnberg, Joannes B. P. A.,Groot, Aede de. "Thermal Rearrangement of Bicyclogermacrane-1,8-dione. Synthesis of Humulenedione and (-)-Cubenol, Starting from Natural (+)-Aromadendrene - V". . p. 4745 - 4754. Retrieved 1994.