128261-61-0

Basic information

• Product Name: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene
• Synonyms: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene
• CAS NO: 128261-61-0
• Molecular Weight: 220.312
• Mol File: 128261-61-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene(128261-61-0)
• EPA Substance Registry System: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene(128261-61-0)

Safety Data

• Hazardous Substances Data: 128261-61-0(Hazardous Substances Data)

Upstream product

• 128261-62-1 (1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one 
• 108-24-7 acetic anhydride 
• 557-34-6 zinc diacetate 
• 80-57-9 (-)-Verbenone 
• 128261-63-2 (1R,3R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>heptane-2-one 
• 137041-01-1 (1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylsulfonyl)-4-vinylbicyclo<3.1.1>heptan-2-one 
• 128261-67-6 (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one 
• 128261-65-4 (1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one 
• 128261-66-5 (1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one 
• 128261-64-3 (1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one 
• 18172-67-3 beta-pinene 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 18309-32-5 Verbenone 
• 128261-63-2 (1R,5S)-3-phenylsulfenyl-6,6-dimethylbicyclo<2.2.1>heptanone 

Downstream Products

• 51371-13-2 (3S,4S)-3-Methyl-4-isopropyl-3-vinyl-1-cyclohexanone 
• 137041-13-5 Methyl <(2R,4S,5S)-2-(4-isopropenyl-5-methyl-5-vinyl-1-oxocyclohexyl)>acetate 
• 137041-14-6 ((4S,5S)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexyl)-acetic acid methyl ester 
• 128261-69-8 (4S,5S)-2-(1-Hydroxy-1-methyl-ethyl)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone 
• 20303-60-0 (4S)-trans-β-elemenone 
• 137041-15-7 ((1R,2R,4S,5S)-2-Hydroxy-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl)-acetic acid methyl ester 
• 126784-59-6 11β-phenylseleno-5,7,8αH-elema-1,3-dien-8,12-olide 
• 137041-17-9 (3S,3aS,5S,6S,7aR)-5-Isopropenyl-6-methyl-3-phenylselanyl-6-vinyl-hexahydro-benzofuran-2-one 
• 137041-18-0 (3R,3aS,5S,6S,7aR)-5-Isopropenyl-6-methyl-3-phenylselanyl-6-vinyl-hexahydro-benzofuran-2-one 
• 1443009-24-2 C₂₁H₂₈N₂O₄S 
• 76015-58-2 onoseriolide 

Relevant articles and documents

Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers

The syntheses of members of a family of lindenane sesquiterpenoid [4+2] dimers led to the total syntheses of sarcandrolide J and shizukaol D. Inspired by a modified biosynthetic pathway, a cascade featuring furan formation/alkene isomerization/Diels–Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules with the correct stereochemistry. This study presents a pioneering synthetic entry to this family of natural products and paves the way for fully exploring their biological functions.

Bioinspired total synthesis of bolivianine: A diels-alder/intramolecular hetero-Diels-Alder cascade approach

We report the first total synthesis of bolivanine in a 14-step pathway involving the synthesis of onoseriolide. Our synthesis features a palladium-catalyzed intramolecular cyclopropanation involving an allylic metal carbene and a Diels-Alder/intramolecular hetero-Diels-Alder cascade, allowing the single-step assembly of a tricyclic system with proper configuration. The synthetic efforts validate our modified biogenetic hypothesis and allow us to confirm the absolute configuration of bolivianine.

A Key Intermediate for the Chiral Synthesis of Elemanoids. Synthesis of (+)-β-Elemenone

(1R,5S)-3-Phenylsulfenyl-6,6-dimethylbicycloheptanone obtained from (+)-nopinone was transformed into (1R,4S,5S)-4-methyl-4-vinylbicycloheptan-2-one, whose cyclobutane ring was cleaved with BF3*EtO2-Zn(OAc)2 in acetic anhydride to provide (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (5), the key intermediate, in a highly regio- and stereoselective manner.Regioselective introduction of a three-carbon unit to 5 with acetone followed by dehydration yielded (+)-β-elemenone.