59415-37-1

Basic information

• Product Name: (S)-tert-butyl 2-phenylpropionate
• Synonyms: (S)-tert-butyl 2-phenylpropionate
• CAS NO: 59415-37-1
• Molecular Weight: 206.285
• Mol File: 59415-37-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (S)-tert-butyl 2-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-phenylpropionate(59415-37-1)
• EPA Substance Registry System: (S)-tert-butyl 2-phenylpropionate(59415-37-1)

Safety Data

• Hazardous Substances Data: 59415-37-1(Hazardous Substances Data)

Upstream product

• 39149-80-9 tert-butyl 2-bromopropionate 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 40058-88-6 tert-butyl 2-chloropropionate 
• 38111-44-3 phenylzinc(II) bromide 
• 100-58-3 phenylmagnesium bromide 
• 108-95-2 phenol 
• 17763-67-6 Phenyl triflate 
• 72658-10-7 tert-butyl trimethylsilyl methyl ketene acetal 
• 20487-40-5 tert-butyl propionate 

Relevant articles and documents

Synthesis method of (S)-2-aryl propionate compound

The invention discloses a synthesis method of a (S)-2-aryl propionate compound. The (S)-2-aryl propionate compound shown in the formula IV is obtained by taking a compound shown in a formula I and a compound shown in a formula II as raw materials and reacting under the conditions of a chiral ligand shown in a formula III, a nickel catalyst, a photocatalyst, a reducing agent and alkali under the condition of visible light. The method has the advantages of cheap and easily available raw materials, convenient generation, mild conditions, environmental protection and safety, the photocatalyst canbe recycled, the production cost is greatly reduced, the test operation is simple, less waste is generated, and the method can be developed into an industrial production method.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents

The first iron-catalyzed enantioselective cross-coupling reaction between an organometallic compound and an organic electrophile is reported. Synthetically versatile racemic α-chloro- and α-bromoalkanoates were coupled with aryl Grignard reagents in the presence of catalytic amounts of an iron salt and a chiral bisphosphine ligand, giving the products in high yields with acceptable and synthetically useful enantioselectivities (er up to 91:9). The produced α-arylalkanoates were readily converted to the corresponding α-arylalkanoic acids with high optical enrichment (er up to >99:1) via simple deprotections/recrystallizations. The results of radical probe experiments are consistent with a mechanism that involves the formation of an alkyl radical intermediate, which undergoes subsequent enantioconvergent arylation in an intermolecular manner. The developed asymmetric coupling offers not only facile and practical access to various chiral α-arylalkanoic acid derivatives, which are of significant pharmaceutical importance, but also a basis of controlling enantioselectivity in an iron-catalyzed organometallic transformation. (Chemical Equation Presented).