28465-10-3

Basic information

• Product Name: (1R)-3β-Isopropenyl-2,2-dimethylcyclobutane-1β-methanol acetate
• Synonyms: (1R)-3β-Isopropenyl-2,2-dimethylcyclobutane-1β-methanol acetate;(1R,3R)-1-Acetoxymethyl-2,2-dimethyl-3-(1-methylethenyl)cyclobutane;[1R,3R,(+)]-2,2-Dimethyl-3-isopropenylcyclobutanemethanol acetate;Acetic acid [(1R)-2,2-dimethyl-3β-isopropenylcyclobutane-1β-yl]methyl ester;(1R,3R)-cis-2,2-Dimethyl-3-isopropenyl-cyclobutanemethanol acetate
• CAS NO: 28465-10-3
• Molecular Formula: C12H20O2
• Molecular Weight: 196.286
• Mol File: 28465-10-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R)-3β-Isopropenyl-2,2-dimethylcyclobutane-1β-methanol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-3β-Isopropenyl-2,2-dimethylcyclobutane-1β-methanol acetate(28465-10-3)
• EPA Substance Registry System: (1R)-3β-Isopropenyl-2,2-dimethylcyclobutane-1β-methanol acetate(28465-10-3)

Safety Data

• Hazardous Substances Data: 28465-10-3(Hazardous Substances Data)

Upstream product

• 473-66-5 cis-(-)-verbanone 
• 22339-08-8 (+)-trans-verbenol 
• 7785-70-8 (+)-α-pinene 
• 675605-82-0 (S)-2-[(1S,3R)-3-hydroxymethyl-2,2-dimethylcyclobutyl]-1,2-propanediol 
• 108-24-7 acetic anhydride 
• 149-73-5 trimethyl orthoformate 
• 28465-09-0 (1R-cis)-1-hydroxymethyl-2,2-dimethyl-3-isopropenyl-cyclobutane 
• 18358-54-8 cis-(-)-2,2-dimethyl-3-(1-methylethenyl)cyclobutanal 
• 28465-11-4 (1R-cis)-(+)-2,2-dimethyl-3-isopropenyl-cyclobutane carboxylic acid 
• 39863-91-7 trans-(R)-verbenol acetate 
• 22571-78-4 (+)-cis-pinononoic acid 
• 71628-89-2 (1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione 
• 177316-71-1 (1R,3S)-(+)-cis-3-acetyl-1-(2-acetoxyethenyl)-2,2-dimethylcyclobutane 
• 93921-54-1 (1R,3S)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid methyl ester 

Relevant articles and documents

ISOLATION, IDENTIFICATION AND SYNTHESIS OF THE SEX PHEROMONE OF THE CITRUS MEALYBUG, PLANOCOCCUS CITRI (RISSO)

The sex attractant pheromone of the citrus mealybug, Planococcus citri (Risso), has been identified as (1R-cis)-(+)-2,2-dimethyl-3-(1-methylethenyl)cyclobutanemethanol acetate (VI).

Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri

The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3-NalO4, and methylenation with Zn/CH 2Br2/TiCl4.

OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS XLIII. SYNTHESIS OF (1R,3R)-(+)-CIS-1-ACETOXYMETHYL-3-ISOPROPENYL-2,2-DIMETHYLCYCLOBUTANE - THE SEX PHEROMONE OF THE VINE MEALY BUG (PLANOCOCCUS CITRI) AND ITS (1S,3S)-(-)-CIS-ENANTIOMER

(1R,3R)-(+)-cis-1-Acetoxymethyl-3-isopropenyl-2,2-dimethylcyclobutane, which is the sex pheromone of the vine mealy bug (Planococcus citri), and its (1S,3S)-(-)-cis-enantiomer were synthesized from (+)- or (-)-α-pinene by ozonolysis in two stages.The overall yield of the required compounds calculated on the initial α-pinenes amounted to about 40percent.