1472-07-7

Basic information

• Product Name: METHYL (R)-3-PHENYLBUTYRATE
• Synonyms: METHYL (R)-BETA-METHYLHYDROCINNAMATE;METHYL (R)-3-PHENYLBUTYRATE;methyl (r)-β-methylhydrocinnamate;(R)-methyl 3-phenylbutanoate
• CAS NO: 1472-07-7
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• Mol File: 1472-07-7.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 234.2°C at 760 mmHg
• Flash Point: 95°C
• Appearance: /
• Density: 1.020 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0537mmHg at 25°C
• Refractive Index: n20/D 1.497
• CAS DataBase Reference: METHYL (R)-3-PHENYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (R)-3-PHENYLBUTYRATE(1472-07-7)
• EPA Substance Registry System: METHYL (R)-3-PHENYLBUTYRATE(1472-07-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1472-07-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O2/c1-9(8-11(12)13-2)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3/t9-/m1/s1

Upstream product

• 3461-39-0 3-phenyl-butyric acid methyl ester 
• 3461-50-5 methyl trans-3-methylcinnamate 
• 67-56-1 methanol 
• 772-14-5 (R)-3-phenylbutyric acid 
• 623-43-8 crotonic acid methyl ester 
• 214759-91-8 N-methoxy-N-methyl-3-phenylbutanamide 
• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 160538-63-6 (4R)-4-phenyl-3-<(3R)-3-phenylbutyryl>oxazolidin-2-one 
• 98-86-2 acetophenone 
• 221878-52-0 (+/-)-3-phenylbutyric acid vinyl ester 
• 4593-90-2 3-phenylbutyric acid 
• 98-80-6 phenylboronic acid 
• 2996-92-1 phenyl trimethylsiloxane 
• 186581-53-3 diazomethane 

Downstream Products

• 772-14-5 (R)-3-phenylbutyric acid 
• 42307-58-4 3-phenylbutanal 
• 135-98-8 (2R)-sec-butylbenzene 
• 221878-55-3 (R)-(-)-vinyl 3-phenylbutanoate 
• 2031-46-1 (R)-3-phenylbutanol 

Relevant articles and documents

An efficient preparative scale resolution of 3-phenylbutyric acid by lipase from Burkholderia cepacia (Chirazyme L1)

Lipase from Burkholderia cepacia (Chirazyme L1) catalysed the highly enantioselective hydrolysis of racemic methyl 3-phenylbutyrate to afford (R)- (-)-methyl 3-phenylbutyrate of >98% ee (E>50). The resolution was performed at 150 g scale yielding 68.7 g of (R)-(-)-methyl 3-phenylbutyrate (>98% ee, 92% yield on enantiomer) and (S)-(+)-3-phenylbutyric acid of 89% ee.

Direct Lewis Acid Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides, and Acids

The identification of Yb(OTf)3 through a multivariable high-throughput experimentation strategy has enabled a unified protocol for the direct conversion of enantioenriched N-acyloxazolidinones to the corresponding chiral esters, amides, and carboxylic acids. This straightforward and catalytic method has shown remarkable chemoselectivity for substitution at the acyclic N-acyl carbonyl for a diverse array of N-acyloxazolidinone substrates. The ionic radius of the Lewis acid catalyst was demonstrated as a key driver of catalyst performance that led to the identification of a robust and scalable esterification of a pharmaceutical intermediate using catalytic Y(OTf)3.

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.