132077-05-5

Basic information

• Product Name: (1aR^*,4aR^*,5R^*,7aR^*,7bS^*)-decahydro-3,3,5,7b-tetramethyl-4aH-cyclopropazulen-4a-ol
• CAS NO: 132077-05-5
• Molecular Weight: 222.371
• Mol File: 132077-05-5.mol

Chemical Properties

• CAS DataBase Reference: (1aR^*,4aR^*,5R^*,7aR^*,7bS^*)-decahydro-3,3,5,7b-tetramethyl-4aH-cyclopropazulen-4a-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR^*,4aR^*,5R^*,7aR^*,7bS^*)-decahydro-3,3,5,7b-tetramethyl-4aH-cyclopropazulen-4a-ol(132077-05-5)
• EPA Substance Registry System: (1aR^*,4aR^*,5R^*,7aR^*,7bS^*)-decahydro-3,3,5,7b-tetramethyl-4aH-cyclopropazulen-4a-ol(132077-05-5)

Safety Data

• Hazardous Substances Data: 132077-05-5(Hazardous Substances Data)

Upstream product

• 74878-87-8 (1aR,2S,7aR,7bR)-2-Bromo-3,3,5,7b-tetramethyl-1a,2,3,4,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulene 
• 107770-62-7 ethyl (1R^*,2R^*,7S^*)-3-<(E)-ethylidene>-1,5,5-trimethylbicyclo<5.1.0>octane-2-acetate 
• 107770-63-8 (1aR^*,7aR^*,7bS^*)-1,1a,2,3,4,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6H-cyclopropazulen-6-one 
• 107770-64-9 (1aR^*,6R^*,7aR^*,7bS^*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-1H-cyclopropazulen-6-ol 
• 107770-66-1 (1aR^*,4aS^*,5R^*,6R^*,7aR^*,7bS^*)-4a,5-epoxydecahydro-3,3,5,7b-tetramethyl-1H-cyclopropazulen-6-ol 
• 107770-61-6 (R)-1-((1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]oct-2-en-3-yl)-ethanol 
• 107770-61-6 (S)-1-((1R,7S)-1,5,5-Trimethyl-bicyclo[5.1.0]oct-2-en-3-yl)-ethanol 
• 104166-08-7 cis-1,5,5-trimethylbicyclo<5.1.0>octan-2-one 
• 104166-05-4 2,5,5-trimethyl-cyclohept-2-en-1-one ethylene ketal 
• 104166-06-5 C₁₃H₂₂O₂ 
• 104166-07-6 2,5,5-trimethylcycloheptan-2-en-1-one 
• 107770-67-2 (1aR^*,4aS^*,7aR^*,7bS^*)-1,1a,2,3,4,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-4aH-cyclopropazulen-4a-ol 
• 42747-41-1 trimethyl-2,5,5-cyclohexene-2-one-1 
• 75-11-6 diiodomethane 

Relevant articles and documents

A short total synthesis of (±)-isoafricanol and two of its isomers

The syntheses of (±)-isoafricanol and two of its isomers were achieved from 2,5,5-trimethylcyclohex-2-en-1-ol. The key step was a photoreductive radical cyclisation of an unsaturated ketone.

Synthetic Approach for (+)-Africanol

Synteses of (+)-africanol (1) and (+)-isoafricanol (2) were attempted by reductive radical cyclization of (1S,2S,8S)-2-(4'-butenyl)-1,5,5-trimethyl-bicyclo-3-octanone derived from (1R,2S,4S,8S)-4-alkoxy-1,6,6-trimethyl-tricyclo2,4>nonane.This cyclization gave (+)-1 and (+)-2 as minor components, together with trans fused epimers as major components.

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.