93132-69-5

Basic information

• Product Name: (1S,3R)-2,2-dimethyl-3-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]cyclopropanecarboxylic acid
• CAS NO: 93132-69-5
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.2164
• Mol File: 93132-69-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 316.1°C at 760 mmHg
• Flash Point: 159.2°C
• Density: 1.187g/cm³
• Vapor Pressure: 8.95E-05mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: (1S,3R)-2,2-dimethyl-3-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R)-2,2-dimethyl-3-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]cyclopropanecarboxylic acid(93132-69-5)
• EPA Substance Registry System: (1S,3R)-2,2-dimethyl-3-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]cyclopropanecarboxylic acid(93132-69-5)

Safety Data

• Hazardous Substances Data: 93132-69-5(Hazardous Substances Data)

Upstream product

• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 35867-05-1 methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate 
• 4638-92-0 (1R,3R)-trans-chrysanthemic acid 
• 827-90-7 trans-chrysanthemic acid 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 27335-33-7 methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate 

Relevant articles and documents

Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods

Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin I and three pyrethrin II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alcohol components [(S)-cinerolone, (S)-jasmololone, and (S)-pyrethrolone] were synthesized: (i) straightforward Sonogashira-type cross-couplings using available (S)-4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-en-1-ones (the prallethrin alcohol) for (S)-cinerolone (overall 52% yield, 98% ee) and (S)-pyrethrolone (overall 54% yield, 98% ee) and (ii) traditional decarboxylative-aldol condensation and lipase-catalyzed optical resolution for (S)-jasmololone (overall 16% yield, 96% ee). Two counter acid segments [(1R,3R)-chrysanthemic acid (A) and (1R,3R)-second chrysanthemic acid precursor (B)] were prepared: (i) C(1) epimerization of ethyl (±)-chrysanthemates and optical resolution using (S)-naphthylethylamine to afford A (96% ee) and (ii) concise derivatization of A to B (96% ee). All six pyrethrin esters (cinerin I/II, jasmolin I/II, and pyrethrin I/II) were successfully synthesized utilizing an accessible esterification reagent (TsCl/N-methylimidazole). To investigate the stereostructure-activity relationship, all four chiral stereoisomers of cinerin I were synthesized. Three alternative syntheses of (±)-jasmololone were investigated (methods utilizing Piancatelli rearrangement, furan transformation, and 1-nitropropene transformation). Insecticidal activity assay (KD50 and IC50) against the common mosquito (Culex pipiens pallens) revealed that (i) pyrethrin I > pyrethrin II, (ii) pyrethrin I (II) > cinerin I (II) ? jasmolin I (II), and (iii) "natural" cinerin I ? three "unnatural" cinerin I compounds (apparent chiral discrimination).