(R)-3-Oxopentan-2-yl benzoate

Base Information

• Chemical Name: (R)-3-Oxopentan-2-yl benzoate
• CAS No.: 460997-47-1
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• DSSTox Substance ID: DTXSID50465423
• Nikkaji Number: J1.764.893D
• Wikidata: Q82291359
• Mol file: 460997-47-1.mol

Synonyms:(R)-3-Oxopentan-2-yl benzoate;460997-47-1;[(2R)-3-oxopentan-2-yl] Benzoate;(2R)-2-(benzoyloxy)-3-Pentanone;(R)-3-Oxopentan-2-ylbenzoate;DTXSID50465423;(2R)-3-Oxopentan-2-yl benzoate;AKOS022173054;A23114

Chemical Property of (R)-3-Oxopentan-2-yl benzoate

Chemical Property:

• PSA: 43.37000
• LogP: 2.21100
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

97% ^*data from raw suppliers

(R)-3-Oxopentan-2-ylbenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C(C)OC(=O)C1=CC=CC=C1
• Isomeric SMILES: CCC(=O)[C@@H](C)OC(=O)C1=CC=CC=C1

Technology Process of (R)-3-Oxopentan-2-yl benzoate

There total 3 articles about (R)-3-Oxopentan-2-yl benzoate 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: 57.0%

(R)-Methyl lactate (17392-83-5,2155-30-8) + ethylmagnesium bromide (925-90-6) + benzoic acid anhydride (93-97-0) → (-)-(R)-3-oxopentan-2-yl benzoate (460997-47-1)

Guidance literature:

(R)-Methyl lactate; With isopropylmagnesium chloride; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; at -20 - 0 ℃; for 1h; Inert atmosphere;

ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 1h; Inert atmosphere;

benzoic acid anhydride; With dmap; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.6b03060

Reference yield:

2-hydroxy-3-pentanone (5704-20-1) + benzoic acid anhydride (93-97-0) → (-)-(R)-3-oxopentan-2-yl benzoate (460997-47-1)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/0040-4039(94)88434-X

Reference yield:

(R)-2-(benzyloxy)pentan-3-one (132489-34-0) → (-)-(R)-3-oxopentan-2-yl benzoate (460997-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran / 15 h / 20 °C

2: (i-Pr)2NEt, DMAP / tetrahydrofuran / 15 h / 20 °C

With dmap; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0040-4039(94)88434-X

upstream raw materials:

2-hydroxy-3-pentanone

benzoic acid anhydride

(R)-2-(benzyloxy)pentan-3-one

(R)-Methyl lactate

Downstream raw materials:

Benzoic acid (1R,3S,4S,5S)-6-benzyloxy-4-hydroxy-1,3,5-trimethyl-2-oxo-hexyl ester

(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

C₆H₅CO₂CH(CH₃)C(C₂H₄)OB(C₆H₁₁)2

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-hydroxy-3,6-dimethyl-7-oxo-nonyl) ester 1-tert-butyl ester