133797-12-3

Basic information

• Product Name: (R)-methyl 2-propionyloxy-2-phenylethanoate
• Synonyms: (R)-methyl 2-propionyloxy-2-phenylethanoate
• CAS NO: 133797-12-3
• Molecular Weight: 222.241
• Mol File: 133797-12-3.mol

Chemical Properties

• CAS DataBase Reference: (R)-methyl 2-propionyloxy-2-phenylethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl 2-propionyloxy-2-phenylethanoate(133797-12-3)
• EPA Substance Registry System: (R)-methyl 2-propionyloxy-2-phenylethanoate(133797-12-3)

Safety Data

• Hazardous Substances Data: 133797-12-3(Hazardous Substances Data)

Upstream product

• 20698-91-3 (R)-methyl mandelate 
• 802294-64-0 propionic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 1195180-97-2 (+/-)-propionyloxy-phenyl-acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1359987-72-6 C₂₂H₃₈O₂Sn 

Relevant articles and documents

Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids

Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).

Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide

Incorporation reactions of carbon dioxide (CO2) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α- amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.

Remote Control of Stereogenicity Transfer by Ring-Generated Anisotropic Orbital Overlap. Stereochemistry of Hydrogen Shift in the Intramolecular Reverse Ene Reaction of a cis-2- Alkyl-1 -alkenylcyclopropane

The thermal rearrangement of cis-2-(2-propyl)-1(E)-propenylcyclopropane at temperatures near 230 °C in the gas phase occurs with activation parameters of Ea = 35.5 ±0.6 kcal/mol and log A = 12.05 ±0.5 (A, s-1). The optically active isotopically doubly labeled analogue (cis-2(S)-(2(S)-propyl-1-d3)-1(S)-(1(E)-propenyl-2-rf)cyclopropane 5 was synthesized in 12 steps from dicyciopentadiene. Pyrolysis of 5 gave only 2-methyl-octa-2(Z),5(Z)-diene-1-d3-7(S)-d, with high stereospecificity at each of the three sites of stereogenicity. This result is the one predicted if the reaction is controlled by optimal overlap ' of the reacting C-H and π bond orbitals with the Cs symmetric component of the degenerate 3E' highest occupied orbital of the cyclopropane ring.