64399-27-5

Usage

Uses

1-(4-Chlorophenyl)cyclopropanecarbonitrile

InChI:InChI=1/C10H8ClN/c11-9-3-1-8(2-4-9)10(7-12)5-6-10/h1-4H,5-6H2

Upstream product

• 106-93-4 ethylene dibromide 
• 140-53-4 p-chlorobenzyl cyanide 
• 96-49-1 [1,3]-dioxolan-2-one 
• 107-04-0 1-Bromo-2-chloroethane 
• 106-39-8 bromochlorobenzene 
• 5500-21-0 cyclopropropanecarbonitrile 
• 72934-37-3 3-(4-chlorophenyl)-1-cyclopropanecarboxylic acid 

Downstream Products

• 72934-37-3 3-(4-chlorophenyl)-1-cyclopropanecarboxylic acid 
• 20401-29-0 α,α-dimethyl-(4-chlorophenyl)acetaldehyde 
• 100845-90-7 1-carboxaldehyde-1-(p-chlorophenyl)-cyclopropane 
• 1039766-08-9 C₂₁H₂₅ClN₂ 
• 1134916-53-2 [1-(4-chloro-phenyl)-cyclopropyl]-quinolin-3-yl-methanone 
• 1017388-59-8 1-(1-(4-chlorophenyl)cyclopropyl)ethan-1-one 
• 1314760-57-0 1-(4-chloro-3-nitrophenyl)cyclopropanecarbonitrile 
• 848846-84-4 methyl 1-(4-chloro-3-nitrophenyl)cyclopropanecarboxylate 
• 848846-85-5 methyl 1-(3-amino-4-chlorophenyl)cyclopropanecarboxylate 
• 236418-11-4 1-(4-chloro-3-nitro-phenyl)-1-cyclopropanecarboxylic acid 
• 1346641-11-9 1-(4-chlorophenyl)-N-(4-cyano-2,3,5,6-tetrafluorophenyl)cyclopropanecarboxamide 
• 78682-33-4 1-(p-chlorophenyl)-1-cyclopropanecarbonyl chloride 
• 1361189-44-7 1-[4-(2-aminopyrimidin-5-yl)phenyl]cyclopropanecarbonitrile 
• 1454654-57-9 1-{4-[5-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarbonitrile 

Relevant academic research and scientific papers

COMPOUNDS FOR TREATING AND PREVENTING GROWTH HORMONE RECEPTOR-DEPENDENT CONDITIONS

The invention relates to compounds, in particular pyrimidine-2,4-diamines, analogues and salts thereof and pharmaceutical compositions comprising pyrimidine-2,4-diamines analogues and salts thereof for use in the treatment and prevention of a disease, in particular a growth hormone receptor-dependent condition. The invention also relates to methods of using these compounds and compositions to treat physiological dsorders related to the amount or activity of growth hormone. In a particular embodiment, the invention relates to a compound according to formula 1 for use in the treatment or prevention of a disease in a subject

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.

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.).

Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles

A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.

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.

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.

Enantioselective C-H Functionalization-Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes

An enantioselective C-H functionalization route to perfluoroalkyl-containing 3-azabicyclo[3.1.0]hexanes is disclosed. A modular and bench-stable diazaphospholane ligand enables highly enantioselective Pd(0)-catalyzed cyclopropane C-H functionalization using trifluoroacetimidoyl chlorides as electrophilic partners. In turn, the resulting cyclic ketimine products react smoothly with a broad variety of nucleophiles in one-pot processes enabling the rapid and modular construction of heavily substituted pyrrolidines.

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.

Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide

A Lewis basic sulfide catalyzed electrophilic bromocyclization of cyclopropylmethyl amide has been developed. The catalytic protocol is applicable to both 1,1- and 1,2-substituted cyclopropylmethyl amides, giving oxazolines and oxazines in good yields and excellent diastereoselectivity.