198022-60-5

Basic information

• Product Name: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid
• Synonyms: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid
• CAS NO: 198022-60-5
• Molecular Weight: 286.328
• Mol File: 198022-60-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(198022-60-5)
• EPA Substance Registry System: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(198022-60-5)

Safety Data

• Hazardous Substances Data: 198022-60-5(Hazardous Substances Data)

Usage

General Description

(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is a chemical compound with a complex structure containing a cyclopentane ring and a carboxylic acid group. It is a chiral compound, with the (1S,2R) configuration. The compound also contains a methylene group and a propenyl oxycarbonyl group, as well as a phenyl group. It is likely to have bioactive properties and may be of interest in medicinal chemistry and drug discovery.

Upstream product

• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 139228-09-4 5-methylenetetrahydrocyclopenta[c]furan-1,3-dione 
• 4534-68-3 1,2,3,4-butanetetracarboxylic acid 
• 4373-15-3 1,2,3,4-butanetetracarboxylic acid tetraethyl ester 
• 90474-14-9 4-Methylene-cyclopentane-1,2-dicarboxylic acid 
• 6261-04-7 2,3,4-tris(ethoxycarbonyl)cyclopentanone 
• 1703-61-3 rac-4-oxocyclopentane-1,2-dicarboxylic acid 
• 914637-96-0 diethyl 4-oxo-1,2-cyclopentanedicarboxylate 
• 343956-49-0 4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester 

Downstream Products

• 198022-62-7 (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate 
• 198022-65-0 (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid 

Relevant articles and documents

Practical syntheses of chiral α-amino acids and chiral half-esters by kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts

The large-scale applications of the kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides (UNCAs) and the desymmetrization of cyclic meso-anhydrides using modified cinchona alkaloids are described. These asymmetric reactions are effective organocatalytic methods for the synthesis of chiral a-amino acids 6 and chiral half-esters 2 on an industrial scale, because the organocatalyst recovery and product purification can be carried out by a simple extractive procedure obviating a chromatographic purification step. The modified cinchona alkaloid catalysts (DHQD) 2AQN and (DHQ)2AQN, as reported by Deng and co-workers, are not readily available and therefore not suitable for industrial-scale synthesis. Various O-alkylated quinidine and quinine derivatives were prepared and screened as catalysts for the kinetic resolution of phenylalanine UNCA with alcohol. The readily prepared O-propargylquinidine (OPQD) and O-propargylquinine (OPQ) were discovered to be highly enantioselective and practical catalysts. These new catalysts were applied to the synthesis of chiral propargylglycine 24 and the key intermediate of BAY10-8888/PLD-118, 26, on an industrial scale, by the kinetic resolution of UNCA 22 and the desymmetrization of cyclic meso-anhydride 25, respectively.

Novel antifungal β-amino acids: Synthesis and activity against Candida albicans

A series of novel β-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. β-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections.