26771-06-2

Basic information

• Product Name: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;(1S)-2,2-Dimethyl-3α-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;(1S)-2β-(2-Methyl-1-propenyl)-3,3-dimethylcyclopropane-1β-carboxylic acid;(1S,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid
• CAS NO: 26771-06-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 247-994-4
• Mol File: 26771-06-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.0088mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-06-2)
• EPA Substance Registry System: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-06-2)

Safety Data

• Hazardous Substances Data: 26771-06-2(Hazardous Substances Data)

Usage

General Description

The chemical "(1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid" is an organic compound with a molecular formula of C11H18O2. It is a cyclopropane carboxylic acid with two methyl groups and an isopropyl group attached to the cyclopropane ring. (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is a colorless liquid at room temperature and is commonly used in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable building block in organic synthesis and medicinal chemistry research.

InChI:InChI=1/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8-/m1/s1

Upstream product

• 10453-89-1 chrysanthemumic acid 
• 872195-22-7 2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid dicyclohexylmethyl ester 
• 78715-54-5 tert-amyl trans-chrysanthemate 
• 627-58-7 2,5-dimethyl-1,5-hexadiene 
• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 2935-23-1 cis-Chrysanthemic acid 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 19165-55-0 2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 75996-53-1 Benzoic acid (E)-5-methoxycarbonyl-1,1,4,4-tetramethyl-pent-2-enyl ester 
• 75996-49-5 2-((E)-4-Hydroxy-1,1,4-trimethyl-pent-2-enyl)-malonic acid dimethyl ester 

Downstream Products

• 2259-14-5 (1S,3S)-trans-chrysanthemic acid 
• 4638-92-0 (1R,3R)-trans-chrysanthemic acid 
• 454-25-1 (+/-)-trans-Homochrysanthemsaeure 
• 497-96-1 (+/-)-trans-(E)-pyrethricsaeure 
• 94672-92-1 (+/-)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r) 
• 56650-12-5 (1S)-cis-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride 
• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 25402-06-6 (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate 
• 121-21-1 pyrethrin I 
• 121-20-0 cinerin II 
• 1172-63-0 jasmolin II 
• 121-29-9 Pyrethrin II 
• 93132-69-5 (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid 
• 1152308-88-7 2,3,5,6-tetrafluorobenzyl (1R)-cis-3-cyano-2,2-dimethylcyclopropane carboxylate 

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).

Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol

2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.

Competing cyclopropane over epoxide formation from γ-halogeno-δ-hydroxy-ketones

Carbocyclization has been selectively achieved over epoxide formation from a γ-chloro-δ-hydroxy-ketone in the presence of a lithiumamide or using a different strategy in which the related silyloxyenol ether bearing an iodine atom at gamma-position and a silyloxy group in delta-position is reacted with tetrabutylammonium fluoride. These approaches take advantage of (i) the poor reactivity of the intermediate β-halogeno lithiumalkoxide first formed in the former case and (ii) the poorer ability of the fluoride ion to desilylate a silyl ether over a silylenol ether.