72934-37-3

Usage

Chemical Properties

White crystalline powder

InChI:InChI=1/C10H9ClO2/c11-8-3-1-7(2-4-8)10(5-6-10)9(12)13/h1-4H,5-6H2,(H,12,13)/p-1

Upstream product

• 140-53-4 p-chlorobenzyl cyanide 
• 64399-27-5 1-(4-chlorophenyl)-1-cyclopropanecarbonitrile 

Downstream Products

• 72934-36-2 1-(4-chlorophenyl)cyclopropane-1-amine 
• 301162-11-8 (R)-1-(4-chlorophenyl)-N-[1-[(hydroxyamino)carbonyl]-2-methylpropyl]-N-methylcyclopropanecarboxamide 
• 407637-83-6 1-(4-Chlorophenyl)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}cyclopropanecarboxamide trifluoroacetate 
• 762298-58-8 1-(4-CHLOROPHENYL)-N-(3-{4-[3-(ISOBUTYRYLAMINO)PHENYL]-1-PIPERIDINYL}PROPYL)CYCLOPROPANECARBOXAMIDE 
• 117252-05-8 methyl 1-(4-chlorophenyl)cyclopropane-1-carboxylate 
• 1140898-81-2 N'-(3-bromopyridin-2-yl)-1-(4-chlorophenyl)cyclopropane-carbohydrazide 
• 1140898-88-9 1-(4-chlorophenyl)-N'-(3-(2-hydroxypropan-2-yl)pyridin-2-yl)cyclopropanecarbohydrazide 
• 1020800-67-2 C₂₇H₂₀Cl₄N₄O₂ 
• 1271656-15-5 C₁₂H₁₄ClNO₂ 
• 851204-80-3 C₁₃H₁₁ClN₂OS 
• 1202256-82-3 C₃₆H₄₀Cl₄N₄O₃Si 
• 1095661-33-8 tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate 
• 1309192-24-2 2-[1-(4-chlorophenyl)cyclopropyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide 
• 1309195-49-0 1-(1-(4-chlorophenyl)cyclopropyl)-2-diazoethanone 

Relevant academic research and scientific papers

Synthesis and stereostructure-activity relationship of novel pyrethroids possessing two asymmetric centers on a cyclopropane ring

2-Methylcyclopropane pyrethroid insecticides bearing chiral cyanohydrin esters or chiral ethers and two asymmetric centers on the cyclopropane ring, were synthesized. These compounds were designed using a “reverse connection approach” between the isopropyl group in Fenvalerate, and between two dimethyl groups in an Etofenprox analogue (the methyl, ethyl form), respectively. These syntheses were achieved by accessible ring opening reactions of commercially available (±)-, (R)-, and (S)-propylene oxides using 4-chlorobenzyl cyanide anion as the crucial step, giving good overall yield of the product with >98% ee. The insecticidal activity against the common mosquito (Culex pipiens pallens) was assessed for pairs of achiral diastereomeric (1R*,2S*)-, (1R*,2R*)-cyanohydrin esters, and (1R*,2S*)-, (1R*,2R*)-ethers; only the (1R*,2R*)-ether was significantly effective. For the enantiomeric (1S,2S)-ether and (1R,2R)-ether, the activity was clearly centered on the (1R,2R)-ether. The present stereostructure?activity relationship revealed that (i) cyanohydrin esters derived from fenvalerate were unexpectedly inactive, whereas ethers derived from etofenprox were active, and (ii) apparent chiral discrimination between the (1S,2S)-ether and the (1R,2R)-ether was observed. During the present synthetic study, we performed alternative convergent syntheses of Etofenprox and novel 4-EtO-type (1S,2S)- and (1R,2R)-pyrethroids from the corresponding parent 4-Cl-type pyrethroids, by utilizing a recently-developed hydroxylation cross-coupling reaction.

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids

A monoprotected aminoethyl amine chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches.

Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts

An efficient and regioselective electrophilic bromolactonization of cyclopropylmethyl diesters using triphenylphosphine sulfide (Ph3PS) or diphenyl selenide (Ph2Se) as the Lewis basic chalcogenide catalyst has been developed. It was observed that Ph3PS favored the formation of anti-diastereomer and yielded the multi-functional γ-lactones. Interestingly, the diastereoselectivity was reversed when using Ph2Se as a catalyst where the syn-product instead of the anti-product was favored. (Figure presented.).

C-3 NOVEL TRITERPENONE WITH C-28 UREA DERIVATIVES AS HIV INHIBITORS

The present invention relates to C-3 novel triterpenone with C-28 urea derivatives of formula (I); or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, W, J and X are as defined herein. The present invention also relates to pharmaceutical compositions comprising compounds of formula (I) useful for the treatment of viral diseases and particularly HIV mediated diseases.

C-3 NOVEL TRITERPENONE WITH C-28 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS

Formula (I) The invention relates to C-3 novel triterpenone with C-28 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

Development of a palladium-catalyzed α-arylation of cyclopropyl nitriles

1,1-Disubstituted aryl cyclopropyl nitriles are useful moieties in biologically active compounds and provide access to a range of cyclopropyl derivatives. Herein, we describe the development of a palladium-catalyzed α-arylation of cyclopropyl, cyclobutyl, and cyclopentyl nitriles that affords these functional groups in one step from a variety of aryl bromides in good to excellent yields. Furthermore, we demonstrate the transformation of aryl cyclopropyl nitriles into aryl trifluoromethyl cyclopropanes.

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes

Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions. These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.

A PROCESS FOR THE PREPARATION OF ARYLCYCLOPROPANE CARBOXYLIC CARBONITRILES, AND COMPOUNDS DERIVED THEREFROM

The present invention relates to an efficient process for preparing an arylcyclopropanecarbonitrile, which involves the use of sulfolane as a solvent.

PROCESS FOR THE PREPARATION OF ARYLCYCLOPROPOANE CARBOXYLIC CARBONITRILES, AND COMPOUNDS DERIVED THEREFROM

The present invention relates to an efficient process for preparing an arylcyclopropanecarbonitrile, which involves the use of sulfolane as a solvent.