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

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

Uses

Used in Organic Synthesis:
(2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester is used as a synthetic building block for the creation of complex organic molecules. Its unique structure and reactivity allow chemists to incorporate it into a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. The compound's versatility in organic synthesis is attributed to its ability to participate in various chemical reactions, such as condensation, substitution, and rearrangement reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester is used as an intermediate in the synthesis of various drug candidates. Its unique structural features make it an attractive starting material for the development of new drugs with potential therapeutic applications. The compound's stability and reactivity enable the synthesis of novel drug molecules with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
(2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester is also utilized in the agrochemical industry for the synthesis of new pesticides, herbicides, and other crop protection agents. Its unique structure and reactivity allow for the development of innovative molecules with improved efficacy, selectivity, and environmental compatibility. The compound's potential applications in this industry include the creation of new active ingredients for pest control and the development of more sustainable and environmentally friendly agrochemical products.
Used in Research and Development:
In the field of research and development, (2S)-4-Oxo-1-(9-phenylfluorenyl)-proline Methyl Ester serves as a valuable tool for studying various aspects of organic chemistry, including reaction mechanisms, stereochemistry, and the development of new synthetic methods. Its unique structural features and reactivity make it an ideal candidate for exploring new reaction pathways and discovering novel synthetic strategies. Additionally, the compound can be used as a reference material for the development and optimization of analytical methods, such as chromatography and mass spectrometry, which are essential tools in the characterization and analysis of complex organic mixtures.

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

• 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.

FLUOROHYDROXYPROLINE DERIVATIVES USEFUL IN THE PREPARATION OF PROTEOLYSIS TARGETED CHIMERAS

There is provided novel small molecule E3 ubiquitin ligase protein binding ligand compounds, and to their utility in PROteolysis Targeted Chimeras (PROTACs), as well as processes for their preparation thereof, and use in medicine. There is particularly provided novel small molecule E3 ubiquitin ligase protein binding inhibitorcompounds based on a fluorohydroxyproline scaffold, to their utility as ligands in synthesizing novel PROTACs, and to synthetic methods therefor.

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

Enantiospecific and stereoselective synthesis of polyhydroxylated pyrrolidines and indolizidines from trans-4-hydroxy-L-proline

We have developed a short, efficient, and stereoselective synthesis of polyhydroxylated pyrrolidine and indolizidine glycosidase inhibitors starting from 4-hydroxy-L-proline. The regio- and stereoselective hydroxylation of an N-Pf-4-oxoproline enolate and the stereoselective reduction of the resulting keto alcohol allowed us to introduce the cis diol present in the target compounds. The different side chains needed to complete the syntheses of the target compounds were introduced by reduction of the ester group of a substituted proline or by reaction of organolithium or organomagnesium reagents with the same group followed by stereoselective reduction of the resulting ketones. Hydrogenolysis of the alcohols thus obtained gave the hydrochlorides of the desired pyrrolidine glycosidase inhibitors, which were obtained in nine steps in overall yields greater than 50%. The indolizidine glycosidase inhibitor 8-epi-swainsonine was also prepared using this approach.

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