(3R)-3-hydroxy-3-phenylpropanoic acid

Base Information

• Chemical Name: (3R)-3-hydroxy-3-phenylpropanoic acid
• CAS No.: 2768-42-5
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 2918199090
• European Community (EC) Number: 681-742-8
• Nikkaji Number: J61.916G
• Wikidata: Q27122299
• Metabolomics Workbench ID: 57617
• Mol file: 2768-42-5.mol

Synonyms:2768-42-5;(3R)-3-hydroxy-3-phenylpropanoic acid;(r)-3-hydroxy-3-phenylpropanoic acid;(R)-(+)-3-HYDROXY-3-PHENYLPROPIONIC ACID;(R)-3-hydroxy-3-phenylpropionic acid;SCHEMBL904476;(+)-3-Phenylhydracrylic acid;CHEBI:51059;AYOLELPCNDVZKZ-MRVPVSSYSA-N;(r)-3-hydroxy-3-phenylpropanoicacid;MFCD00145219;AS-64780;Benzenepropanoic acid, b-hydroxy-, (bR)-;(r)-(+)-3-hydroxy-3-phenylpropanoic acid;CS-0207172;Hydrocinnamic acid, .beta.-hydroxy-, (R)-;Benzenepropanoic acid, .beta.-hydroxy-, (R)-;EN300-125238;Benzenepropanoic acid, beta-hydroxy-, (betaR)-;Q27122299;(R)-(+)-3-hydroxy-3-phenylpropionic acid, AldrichCPR

Chemical Property of (3R)-3-hydroxy-3-phenylpropanoic acid

Chemical Property:

• Appearance/Colour: colorless to white crystalline powder or needles
• Vapor Pressure: 7.14E-05mmHg at 25°C
• Melting Point: 116-119 °C
• Refractive Index: 1.575
• Boiling Point: 329.4 °C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 167.2 °C
• PSA: 57.53000
• Density: 1.262 g/cm³
• LogP: 1.19470
• Storage Temp.: 0-6°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-3-Hydroxy-3-phenylpropionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CC(=O)O)O
• Uses: It is employed in the synthesis and evaluation of a novel, reusable solid-supported open chain chiral auxiliary derived from m-hydrobenzoin for the diastereoselective reduction of α-keto esters.

Technology Process of (3R)-3-hydroxy-3-phenylpropanoic acid

There total 85 articles about (3R)-3-hydroxy-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: 97.0%

(S)-3-[(R)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one (1375257-37-6) → (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one (1375257-29-6) + (R)-3-phenyl-3-hydroxypropionic acid (2768-42-5,40620-59-5)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; for 2h; Reflux;

DOI:10.1021/ol300949s

Reference yield: 96.0%

N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o1,5]decane (226067-50-1) → (R)-3-phenyl-3-hydroxypropionic acid (2768-42-5,40620-59-5)

Guidance literature:

N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane; With water; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

With aluminium amalgam; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo000124u

Reference yield: 94.0%

(R)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-3-phenyl-propan-1-one (192648-23-0) → (R)-3-phenyl-3-hydroxypropionic acid (2768-42-5,40620-59-5)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1021/jo961953b

upstream raw materials:

brucine

3-hydroxy-3-phenylpropanoic acid

(R)-3-phenyl-3-hydroxypropanal

2-bromo-3-hydroxy-3-phenyl-propanoic acid

Downstream raw materials:

Cinnamic acid

ethyl (3R)-3-hydroxy-3-phenylpropionate

(R)-3-chloro-3-phenyl-propionic acid ethyl ester

(S)-3-chloro-3-phenyl-propionic acid ethyl ester

Refernces

• 1、 Ribeiro, Carlos Magno R.,Passaroto, Elisa N.,Brenelli, Eugênia C.S.. "Ultrasound in enzymatic resolution of ethyl 3-hydroxy-3-phenylpropanoate". . p. 6477 - 6479. Retrieved 2001.
• 2、 Fujita, Taiki,Kanai, Motomu,Mitsunuma, Harunobu,Sameera, W. M. C.,Yamane, Mina. "Siloxy Esters as Traceless Activators of Carboxylic Acids: Boron-Catalyzed Chemoselective Asymmetric Aldol Reaction**". supporting information. p. 24598 - 24604. Retrieved 2021/10/14.
• 3、 Lorente, Adriana,Pellicena, Miquel,Romea, Pedro,Urpí, Fèlix. "Stereoselective acetate aldol reactions of α-silyloxy ketones". . p. 1023 - 1035. Retrieved 2015/01/30.