2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester

Base Information

• Chemical Name: 2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester
• CAS No.: 364634-27-5
• Molecular Formula: C₁₆H₂₃BO₄
• Molecular Weight: 290.167
• Mol file: 364634-27-5.mol

Synonyms:2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester

Chemical Property of 2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester

Chemical Property:

• PSA: 75.99000
• LogP: 2.01460

Purity/Quality:

99%min ^*data from raw suppliers

2-METHOXYCARBONYL-1-PHENYLETHYLBORONIC ACID PINACOL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester

There total 29 articles about 2-Methoxycarbonyl-1-phenylethylboronic acid pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

bis(pinacol)diborane (73183-34-3) + methyl cinnamate (103-26-4,1754-62-7) → (R)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (364634-27-5) + (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-27-0,364634-27-5)

Guidance literature:

With C₃₄H₂₅N₂⁽¹⁺⁾*Cl^(1-); copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; Reagent/catalyst; enantioselective reaction;

Reference yield: 99.0%

bis(pinacol)diborane (73183-34-3) + methyl cinnamate (103-26-4,1754-62-7) → (R)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (364634-27-5) + (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-27-0,364634-27-5)

Guidance literature:

With C₃₄H₂₅N₂⁽¹⁺⁾*Cl^(1-); copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; Reagent/catalyst; enantioselective reaction;

Reference yield: 99.0%

methyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate → (R)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (364634-27-5)

Guidance literature:

With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; hydrogen; nickel diacetate; at 80 ℃; for 48h; under 60804.1 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.9b00994

upstream raw materials:

bis(pinacol)diborane

methyl cinnamate

2,3-dimethyl-2,3-butane diol

8-(3-methoxy-3-oxo-1-phenylpropyl)hexahydro-1,3,2-oxazaborolo[2,3-b]-1,3,2-oxazaborol-4-ium-8-uide

Downstream raw materials:

methyl (S)-3-hydroxy-3-phenylpropionate

Refernces

• 1、 Aponick, Aaron,Dahiya, Gaurav,Pappoppula, Mukesh. "Configuration Sampling With Five-Membered Atropisomeric P,N-Ligands". supporting information. p. 19604 - 19608. Retrieved 2021/08/13.
• 2、 Liu, Gang,Li, Anqi,Qin, Xueyuan,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu. "Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation". supporting information. p. 2844 - 2848. Retrieved 2019/04/26.