160882-76-8

Basic information

• Product Name: (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester
• Synonyms: (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester;4-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-
• CAS NO: 160882-76-8
• Molecular Formula: C₂₅H₂₁NO₃
• Molecular Weight: 383.43914
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 160882-76-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 515.6°C at 760 mmHg
• Flash Point: 265.6°C
• Appearance: /
• Density: 1.284g/cm³
• Vapor Pressure: 9.73E-11mmHg at 25°C
• Refractive Index: 1.653
• Solubility: Chloroform, Diethyl Ether
• PKA: 1.34±0.40(Predicted)
• CAS DataBase Reference: (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester(160882-76-8)
• EPA Substance Registry System: (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester(160882-76-8)

Safety Data

• Hazardous Substances Data: 160882-76-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester (cas# 160882-76-8) is a compound useful in organic synthesis.

InChI:InChI=1/C25H21NO3/c1-29-24(28)23-15-18(27)16-26(23)25(17-9-3-2-4-10-17)21-13-7-5-11-19(21)20-12-6-8-14-22(20)25/h2-14,23H,15-16H2,1H3/t23-/m0/s1

Upstream product

• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 
• 108-86-1 bromobenzene 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 25603-67-2 9-phenyl-fluoren-9-ol 
• 486-25-9 9-fluorenone 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 179990-59-1 (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 126891-27-8 (2S,3S,4S)-3-methylenecarboxy-4-phenylpyrrolidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of Kainoids and C4 Derivatives

A unified stereoselective synthesis of 4-substituted kainoids is reported. Four kainic acid analogues were obtained in 8-11 steps with up to 54% overall yields. Starting from trans-4-hydroxy-l-proline, the sequence enables a late-stage modification of C4 substituents with sp2 nucleophiles. Stereoselective steps include a cerium-promoted nucleophilic addition and a palladium-catalyzed reduction. A 10-step route to acid 21a was also established to enable ready functionalization of the C4 position.

Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands

(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. This journal is

Asymmetric Synthesis of 3S, 4R-Dihydroxypyrrolidines by Regio- and Stereoselective Hydroxylation of 4-Oxoproline Enolate

A short, efficient and stereoselective synthesis of enantiomerically pure (2R,3S,4R) 3,4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L-proline is presented.The key steps are the regio- and stereoselective hydroxylation