(+)-Bicyclohumulenone

Base Information

• Chemical Name: (+)-Bicyclohumulenone
• CAS No.: 71493-03-3
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 71493-03-3.mol

Synonyms:(E)-(1S,10S)-1,5,8,8-Tetramethyl-bicyclo[8.1.0]undec-5-en-2-one;

Chemical Property of (+)-Bicyclohumulenone

Chemical Property:

• PSA: 17.07000
• LogP: 4.12820

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Bicyclohumulenone

There total 52 articles about (+)-Bicyclohumulenone 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: 90.0%

trimethylsulphoxonium iodide (1030268-24-6) + (2E,7E)-2,5,5,8-Tetramethyl-cyclodeca-2,7-dienone (122470-59-1) → (+/-)-bicyclohumulenone (71493-03-3,74923-32-3,77480-09-2)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 0 ℃;

DOI:10.1021/jo00279a008

Reference yield: 88.0%

(E)-(1R,2S,10R)-1,5,8,8-Tetramethyl-bicyclo[8.1.0]undec-5-en-2-ol (71869-16-4,74034-45-0,74923-31-2) → (+/-)-bicyclohumulenone (71493-03-3,74923-32-3,77480-09-2)

Guidance literature:

Collins oxidation;

DOI:10.1016/0040-4039(80)80152-3

Reference yield:

4-chloro-2-methyl-2-buten-1-al neopentyl acetal (62285-88-5) → (+/-)-bicyclohumulenone (71493-03-3,74923-32-3,77480-09-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1. NaH, 2.) K₂CO₃ / 1.) THF 2.) acetone, reflux

2: 65 percent / LiAlH₄

4: 75 percent / lithium triethylborohydride

5: 2.) acetone, 25 deg C

8: 90 percent / NaH / dimethylsulfoxide / 0 °C

With lithium aluminium tetrahydride; sodium hydride; lithium triethylborohydride; potassium carbonate; In dimethyl sulfoxide;

DOI:10.1021/jo00279a008

upstream raw materials:

trimethylsulphoxonium iodide

(2E,7E)-2,5,5,8-Tetramethyl-cyclodeca-2,7-dienone

(E)-(1R,2S,10R)-1,5,8,8-Tetramethyl-bicyclo[8.1.0]undec-5-en-2-ol

4-chloro-2-methyl-2-buten-1-al neopentyl acetal

Refernces

• 1、 Fukuyama, Yoshiyasu,Hirono, Motoko,Kodama, Mitsuaki. "Total Synthesis of (+)-Bicyclohumulenone". . p. 167 - 170. Retrieved 2007/10/02.
• 2、 Shirahama, H.,Hayano, K.,Kanemoto, Y.,Misumi, S.,Ohtsuka, T.,et al.. "CONFORMATIONALLY SELECTIVE TRANSANNULAR CYCLIZATION OF HUMULENE 9,10-EPOXIDE. SYNTHESIS OF THE TWO SKELETALLY DIFFERENT CYCLOHUMULANOIDS: DL-BICYCLOHUMULENONE AND DL-AFRICANOL". . p. 4835 - 4838. Retrieved 2007/10/02.