2259-14-5

Basic information

• Product Name: (1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: (1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;4-09-00-00169 (Beilstein Handbook Reference);(1S)-2,2-Dimethyl-3β-(2-methyl-1-propenyl)cyclopropane-1α-carboxylic acid;[1S,3S,(-)]-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane-1-carboxylic acid;[1S,3S,(-)]-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;2,2-Dimethyl-3β-(2-methyl-1-propenyl)cyclopropane-1α-carboxylic acid;(1S,3S)-2,2-diMethyl-3-(2-Methylprop-1-en-1-yl)cyclopropanecarboxylic acid;l-trans-Form
• CAS NO: 2259-14-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 218-858-1
• Mol File: 2259-14-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 17-21°
• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.077g/cm³
• Refractive Index: 1.546
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(2259-14-5)
• EPA Substance Registry System: (1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(2259-14-5)

Safety Data

• Hazardous Substances Data: 2259-14-5(Hazardous Substances Data)

Usage

General Description

(1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is a chemical compound with a cyclopropane ring and carboxylic acid functionality. It is a chiral compound, with the (1S-trans) configuration indicating the stereochemistry of the molecule. The presence of the cyclopropane ring and the unsaturated side chain make it a structurally interesting compound with potential applications in organic synthesis and pharmaceutical research. The compound's unique structure may also make it useful as a starting material for the synthesis of other complex molecules. Its specific properties and potential uses could be further explored in the context of its chemical and biological activities.

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

• 827-90-7 trans-chrysanthemic acid 
• 5460-63-9 chrysanthemumic acid methyl ester 
• 494846-49-0 (-)-trans-(1S,3S)-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 627-58-7 2,5-dimethyl-1,5-hexadiene 
• 13899-97-3 (+/-)-3t-(β-chloro-isobutyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid 
• 61057-36-1 (+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 
• 19902-09-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 2163-51-1 (+/-)-3t-(β-hydroxy-isobutyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 19165-55-0 2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 

Downstream Products

• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 26770-95-6 (1S)-trans-chrysanthemumic acid-chloride 
• 94672-92-1 (1S)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r) 
• 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) 
• 29172-41-6 trans-chrysanthemyl acetate 
• 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 

Relevant articles and documents

Identification of the catalytic residues of carboxylesterase from arthrobacter globiformis by diisopropyl fluorophosphate-labeling and site-directed mutagenesis

The role of amino acid residues in the enzymatic activity of carboxylesterase from Arthrobacter globiformis was analyzed by diisopropyl fluorophosphate (DFP) labeling and site-directed mutagenesis. The electrospray ionization mass spectrometric (ESI-MS) analysis of the esterase, covalently labeled by DFP, showed stoichiometric incorporation of the inhibitor into the enzyme. The further comparison of endopeptidase-digested fragments between native and DFP-labeled esterase by fast atom bombardment mass spectrometric (FAB-MS) analysis as well as site-directed mutagenesis indicated that Ser59 in the consensus sequence Ser-X-X-Lys, which is conserved exclusively in penicillin-binding proteins and some esterases, served as a catalytic nucleophile. In addition, the results obtained from analysis of the mutants at position 62 suggested the importance of the basic amino acid side chain at this position, and suggested the significance of this residue acting directly as a general base rather than its involvement in the maintenance of the optimum hydrogenbonding network at the active site.

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).

Lewis Acid Catalyzed Enantioselective Photochemical Rearrangements on the Singlet Potential Energy Surface

The oxadi-methane rearrangement of 2,4-cyclohexadienones to bicyclic ketones was found to proceed with high enantioselectivity (92-97% ee) in the presence of catalytic amounts of a chiral Lewis acid (15 examples, 52-80% yield). A notable feature of the transformation is the fact that it proceeds on the singlet hypersurface and that no triplet intermediates are involved. Rapid racemic background reactions were therefore avoided, and the catalyst loading could be kept low (10 mol %). Computational studies suggest that the enantioselectivity is determined within a Lewis acid bound singlet intermediate via a conical intersection. The utility of the method was demonstrated by a concise synthesis of the natural product trans-chrysanthemic acid.