1265476-80-9

Usage

Structure

Cyclopropanecarbonitrile derivative with a three-membered cyclopropyl ring attached to a phenyl group with chloro and fluoro substituents.

Functional groups

Cyano (C≡N), Chloro (-Cl), and Fluoro (-F) groups.

Application

Primarily used in medicinal chemistry as a building block for the synthesis of various pharmaceuticals and bioactive molecules.

Importance

Unique structural features and reactivity make it an important intermediate in organic synthesis, playing a key role in the development of new drugs and biologically active compounds.

Reactivity

The presence of the cyano group makes it a valuable starting material for the preparation of diverse functionalized cyclopropanes and heterocyclic compounds with potential applications in various industries.

Upstream product

• 251570-03-3 2-(4-chloro-3-fluorophenyl)acetonitrile 
• 107-04-0 1-Bromo-2-chloroethane 
• 106-93-4 ethylene dibromide 

Downstream Products

• 1252641-41-0 (4R)-1-{[1-(4-chloro-3-fluorophenyl)cyclopropyl]carbonyl}-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-L-prolinamide 
• 1268445-06-2 (4R)-1-{[1-(4-chloro-3-fluorophenyl)cyclopropyl]carbonyl}-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-L-prolinamide 
• 1268444-83-2 1-(4-chloro-3-fluorophenyl)cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

CARBOXY DERIVATIVES WITH ANTIINFLAMMATORY PROPERTIES

The invention relates to compounds of formula (I) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: (I) wherein, RA1, RA2, RC and RD are as defined herein.

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.

Systematic investigation of halogen bonding in protein-ligand interactions

Halogen bonding triggers activity: Increasing binding affinity was observed for a series of covalent human Cathepsin L inhibitors by exchanging an aryl ring H atom with Cl, Br, and I, which undergo halogen bonding with the C=O group of Gly61 in the S3 pocket of the enzyme. Fluorine, in contrast, strongly avoids halogen bonding (see scheme). The strong distance and angle dependence of halogen bonding was confirmed for biological systems. Copyright