(2R)-2-methyl-3-phenylpropanoic acid

Base Information

• Chemical Name: (2R)-2-methyl-3-phenylpropanoic acid
• CAS No.: 14367-67-0
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• European Community (EC) Number: 862-637-8
• Nikkaji Number: J70.840B
• Mol file: 14367-67-0.mol

Synonyms:(2R)-2-methyl-3-phenylpropanoic acid;14367-67-0;(R)-2-Methyl-3-phenylpropionic acid;(R)-2-Benzylpropanoic acid;SCHEMBL265577;MCIIDRLDHRQKPH-MRVPVSSYSA-N;alpha(R)-methylbenzenepropionic acid;(2R)-2-methyl-3-phenylpropanoicacid;EN300-212803

Chemical Property of (2R)-2-methyl-3-phenylpropanoic acid

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: C[C@H](CC1=CC=CC=C1)C(=O)O

Technology Process of (2R)-2-methyl-3-phenylpropanoic acid

There total 192 articles about (2R)-2-methyl-3-phenylpropanoic acid 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%

2-Benzyl-2-propenoic acid (5669-19-2) → 2-methyl-3-phenylpropionic acid (1009-67-2,5628-72-8,14367-54-5,14367-67-0)

Guidance literature:

With C₄₈H₅₀Cl₄N₂O₂P₂Ru₃; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 24h; under 3750.38 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.6b00748

Reference yield: 97.0%

(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone (181431-20-9) → 2-methyl-3-phenylpropionic acid (14367-67-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Guidance literature:

(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone; With ytterbium(III) triflate; In methanol; for 3h;

With lithium hydroxide; In tetrahydrofuran; water; for 2h;

DOI:10.1021/acs.joc.8b02451

Reference yield: 97.0%

2-methyl-3-phenylacrylic acid (1895-97-2) → 2-methyl-3-phenylpropionic acid (1009-67-2,5628-72-8,14367-54-5,14367-67-0)

Guidance literature:

With C₄₂H₄₈CoP₂; hydrogen; triethylamine; zinc; In methanol; at 50 ℃; for 16h; under 25858.1 Torr; Reagent/catalyst; Solvent; Temperature; enantioselective reaction;

DOI:10.1021/jacs.9b13876

upstream raw materials:

2-methyl-3-phenylpropanoic acid

2-methyl-3-phenylacrylic acid

methyl (2R)-2-methyl-3-phenylpropanoate

benzyl bromide

Downstream raw materials:

(R)-α-methylhydrocynnamic acid chloride

dexamfetamine

(2S)-2-Methyl-3-phenylpropanoic acid chloride

(-)-(R)-methylbenzylacetohydroxamic acid

Refernces

• 1、 Bezmer,Brown. "". . p. 583,584. Retrieved 1971.
• 2、 Fu, Kaiyue,Ma, Yu,Sun, Yaxin,Tang, Bo,Yang, Guang,Yang, Peng,Yue, Jieyu,Zhang, Li,Zhou, Jianrong Steve. "Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens". supporting information. . Retrieved 2021/11/22.
• 3、 Chirik, Paul J.,Shevlin, Michael,Zhong, Hongyu. "Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage". supporting information. . Retrieved 2020/03/13.