71493-03-3

Basic information

• Product Name: (+)-Bicyclohumulenone
• Synonyms: (+)-Bicyclohumulenone;(1S,5E,10S)-1,5,8,8-Tetramethylbicyclo[8.1.0]undec-5-en-2-one;(1β,5E)-3,3,6,10α-Tetramethylbicyclo[8.1.0]undec-5-en-9-one;1-Acripruninone;Bicyclohumulenone;Bicyclohumulone
• CAS NO: 71493-03-3
• Molecular Formula: C15H24O
• Molecular Weight: 220.35
• Mol File: 71493-03-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Bicyclohumulenone(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Bicyclohumulenone(71493-03-3)
• EPA Substance Registry System: (+)-Bicyclohumulenone(71493-03-3)

Safety Data

• Hazardous Substances Data: 71493-03-3(Hazardous Substances Data)

Upstream product

• 62285-88-5 4-chloro-2-methyl-2-buten-1-al neopentyl acetal 
• 73981-46-1 Acetic acid (E)-(1R,2R,9S,10R)-9-hydroxy-3,3,6,10-tetramethyl-bicyclo[8.1.0]undec-5-en-2-yl ester 
• 139259-38-4 2-[(1R,2S)-2-(4-Methoxy-benzyloxymethyl)-2-methyl-cyclopropylmethylene]-malonic acid dimethyl ester 
• 139259-39-5 2-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-2-methyl-cyclopropylmethyl]-malonic acid dimethyl ester 
• 139259-36-2 (S)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-2-methyl-cyclopropyl]-2,2-dimethyl-[1,3]dioxolane 
• 139259-46-4 (E)-(1S,10S)-1,5,8,8-Tetramethyl-4-phenylsulfanyl-bicyclo[8.1.0]undec-5-en-2-ol 
• 139259-35-1 (S)-4-[(E)-3-(4-Methoxy-benzyloxy)-2-methyl-propenyl]-2,2-dimethyl-[1,3]dioxolane 
• 139259-45-3 (1S,2S)-1-Methyl-2-((E)-2,2,5-trimethyl-6-phenylsulfanyl-hex-4-enyl)-cyclopropanecarbaldehyde 
• 139290-32-7 2-[(1S,2S)-1-Methyl-2-((E)-2,2,5-trimethyl-6-phenylsulfanyl-hex-4-enyl)-cyclopropyl]-oxirane 
• 139259-44-2 [(1S,2S)-1-Methyl-2-((E)-2,2,5-trimethyl-6-phenylsulfanyl-hex-4-enyl)-cyclopropyl]-methanol 
• 139259-37-3 (1S,2S)-2-(4-Methoxy-benzyloxymethyl)-2-methyl-cyclopropanecarbaldehyde 
• 139259-62-4 ((E)-4-Chloro-2-methyl-but-2-enylsulfanyl)-benzene 
• 108404-41-7 (E)(S)-4-(3-hydroxy-2-methylpropenyl)-2,2-dimethyl[1,3]dioxolane 
• 24529-80-4 (E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol 

Relevant articles and documents

Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane- derived ligand and Zn(CH2I)2 was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis

Total Synthesis of (+)-Bicyclohumulenone

(+)-Bicyclohumulenone, a bicyclic sesquiterpene isolated from liverworts, was synthesized using stereoselective Simmons-Smith cyclopropanation and intramolecular alkylation of α-sulfenyl carbanion as key steps.

Stereoselective Cyclopropanation of the 10-Membered Enone. Total Synthesis of Bicyclohumulenone

The stereoselective synthesis of bicyclohumulenone and a discusion of the diastereoselectivity of the cylopropanation based on MM2 calculations are presented.

CONFORMATIONALLY SELECTIVE TRANSANNULAR CYCLIZATION OF HUMULENE 9,10-EPOXIDE. SYNTHESIS OF THE TWO SKELETALLY DIFFERENT CYCLOHUMULANOIDS: DL-BICYCLOHUMULENONE AND DL-AFRICANOL

Two cyclohumulanoids, dl-bicyclohumulenone (4) and dl-africanol (7) were synthetized through newly developed conformationally selective transannular cyclization of humulene 9,10-epoxide (2).The epoxide 2 was converted to a bicyclohumulenediol diacetate 3a in 70percent yield by treatment with BF3.Et2O-Ac2O, while treatment of 2 with trimethylsilyl trifluoromethansulfonate gave an africen-ol (5a and 5b) in 80percent yield.The two intermediates 3a and 5a furnished the natural products 4 and 7 in 30 and 8 percent yield from 2 respectively.