144838-82-4

Basic information

• Product Name: 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE
• Synonyms: 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE;(R)-4-BENZYL-3-(2-PHENYLACETYL)OXAZOLIDIN-2-ONE;(4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one
• CAS NO: 144838-82-4
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.336
• Mol File: 144838-82-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE(144838-82-4)
• EPA Substance Registry System: 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE(144838-82-4)

Safety Data

• Hazardous Substances Data: 144838-82-4(Hazardous Substances Data)

Usage

Description

3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE, also known as (4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one, is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique molecular structure, which contributes to its potential applications in the medical field.

Uses

Used in Pharmaceutical Industry:
3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE is used as an intermediate in the synthesis of (+)-ar-Turmerone (T897275) for its anti-tumor and immune-activating properties. 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE maintains a cytotoxic effect in cancer cells, making it a valuable component in the development of cancer treatments.
Used in Antimicrobial Applications:
3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE also serves as an antimicrobial agent, providing a potential solution for combating various microbial infections. Its ability to inhibit the growth of harmful microorganisms makes it a useful compound in the development of new antimicrobial drugs and therapies.

Upstream product

• 103-82-2 phenylacetic acid 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 864658-42-4 2,2-dimethylpropanoicphenylacetic anhydride 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 378185-97-8 (2R)-1-[(4R)-4-Benzyl-2-oxo-1,3-oxazolan-3-yl]-3-(4-tert-butyldimethylsilyloxy-2,6-dimethylphenyl)-2-phenylpropan-1-one 
• 225089-81-6 (4R)-4-benzyl-3-[(2R)-2,3-diphenylpropanoyl]-1,3-oxazolidin-2-one 
• 17040-62-9 (R)-2,3-diphenylpropanoic acid 
• 1332709-27-9 (4R)-4-benzyl-3-(2-(1-methyl-1H-indol-3-yl)-2-phenylacetyl)oxazolidin-2-one 
• 1332709-23-5 (4R)-4-benzyl-3-(2-bromo-2-phenylacetyl)oxazolidin-2-one 
• 1049037-03-7 C₂₈H₂₇NO₅ 
• 919285-81-7 C₂₈H₂₇NO₅ 
• 1049036-89-6 C₂₇H₂₅NO₄ 
• 919285-80-6 C₂₇H₂₅NO₄ 
• 1049037-04-8 C₂₈H₂₇NO₄ 
• 1049037-05-9 C₂₈H₂₇NO₄ 

Relevant articles and documents

A precisely positioned chiral center in an: I, i + 7 tether modulates the helicity of the backbone peptide

In some cases, helical peptides stabilized by an i, i + 7 tether exhibit better target binding and cellular functions compared to their i, i + 4 analogues. Herein, we carried out a systematic study of the effects of an in-tether chiral center on the i, i + 7 system. We screened the optimal cross linking mode, tether length, in-tether chiral center positions, and absolute configurations. From these studies, we determined that a chiral center of R absolute configuration at the γ-position to the C-terminal of a 10-membered tether could function to efficiently induce helicity of the backbone peptides. This is an important addition to the current i, i + 4 in-tether chiral center induced helicity strategy (CIH strategy), and could have broad biological applications.

Carbon-carbon bond-forming reactions of α-carbonyl carbocations: Exploration of a reversed-polarity equivalent of enolate chemistry

Carbon-carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid- or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an 'umpolung' of conventional enolate chemistry, and enables C-C bond construction in both intra- and intermolecular contexts. Attempts to develop diastereoselective variants of this process using chiral ester and oxazolidinone-based auxiliaries are discussed.

Stereospecific syntheses of 2-alkyl and 2-phenyl substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids

Stereospecific syntheses of 2-methyl-, 2-ethyl-, 2-cyclohexyland 2-phenyl- substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids were developed. The key steps for the formation of the stereogenic centers involved the utilization of Evans' 4-benzyl-2-oxazolidinone chiral auxiliary. These compounds were designed to replace the N-terminal tyrosine residue in opioid peptides.