1802-02-4

Basic information

• Product Name: ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• CAS NO: 1802-02-4
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• Mol File: 1802-02-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 240.8°C at 760 mmHg
• Flash Point: 84.4°C
• Density: 0.991g/cm³
• Vapor Pressure: 0.0372mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate(1802-02-4)
• EPA Substance Registry System: ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate(1802-02-4)

Safety Data

• Hazardous Substances Data: 1802-02-4(Hazardous Substances Data)

Upstream product

• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 15874-80-3 3-methyl-1-(phenylsulfonyl)but-2-ene 
• 64-17-5 ethanol 
• 473-50-7 pyrocin 
• 594-16-1 2,2-dibromopropane 
• 54542-32-4 ethyl (E)-5-methyl-2,4-hexadienoate 
• 623-73-4 diazoacetic acid ethyl ester 
• 3907-06-0 3,3-Dimethylcyclopropen 
• 60066-71-9 (E)-3,3,6-Trimethyl-hept-4-enoic acid ethyl ester 
• 60703-31-3 2,5-dimethyl-2-hexen-4-ol 
• 13905-13-0 2,5-dimethyl-hex-4-en-3-one 
• 84524-95-8 Aethyl-3-(1-chlor-1-methylaethyl)-5-methyl-4-hexenoat 
• 2321-41-7 (1S,3R)-2,2-Dimethyl-3-(2-methyl-allyl)-cyclopropanecarboxylic acid ethyl ester 

Downstream Products

• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 827-90-7 trans-chrysanthemic acid 
• 2259-14-5 (1S,3S)-trans-chrysanthemic acid 
• 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 
• 29182-49-8 6-(1,1-dimethyl-allyl)-4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine 
• 29172-41-6 trans-chrysanthemyl acetate 
• 107821-18-1 3-(1,1-Dimethyl-allyl)-5-methyl-cyclohex-4-ene-1,2-dicarboxylic acid 
• 41884-28-0 (R)-(+)-Tetrahydrolavandulol 
• 4638-92-0 (1R,3R)-trans-chrysanthemic acid 

Relevant articles and documents

Synthesis Method of Cyclopropane or Cyclopentene Derivatives via Fe-catalyzed Cationic Radical Cycloaddition Reaction

In this disclosure Fe (III) complex is used as an electron oxidizing agent to oxidize an electron - rich alkene compound to form a radical cation intermediate, and then a cyclopropane compound or 3 5-membered ring compound is synthesized by inducing a cycloaddition reaction with the diazo compound.

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).

Preparing method of cis, trans-ethyl 2, 2-dimethyl-3-(1-isobutenyl)cyclopropane-1-carboxylate

The invention discloses a method of preparing cis, trans-ethyl 2,2-dimethyl-3-(1-isobutenyl)cyclopropane-1-carboxylate, comprising of making the ethyl glycinate hydro and sodium nitrite in the solvent diazo-react without additional addition of organic acid or mineral acid to get ethyl diazoacetate which is to react with the 2,5-Dimethyl-2,4-hexadiene under the catalyst effect and then be desolvated and rectificated to get ethyl chrysanthemumate.The invention is easy to use with high production yield and high contents.