(S)-2-amino-3-cyclohexylpropanoic acid

Base Information

• Chemical Name: (S)-2-amino-3-cyclohexylpropanoic acid
• CAS No.: 27527-05-5
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Hs Code.: 2922499990
• European Community (EC) Number: 839-318-7
• UNII: GYR4SF0FVQ
• DSSTox Substance ID: DTXSID60351883
• Nikkaji Number: J88.501K
• Wikidata: Q27093850
• ChEMBL ID: CHEMBL383208
• Mol file: 27527-05-5.mol

Synonyms:cyclohexylalanine;cyclohexylalanine hydrochloride;cyclohexylalanine, (+-)-isomer;cyclohexylalanine, (R)-isomer;cyclohexylalanine, (S)-isomer;L-cyclohexylalanine

Chemical Property of (S)-2-amino-3-cyclohexylpropanoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 322 °C
• Refractive Index: 1.489
• Boiling Point: 307.147 °C at 760 mmHg
• PKA: 2.33±0.10(Predicted)
• Flash Point: 139.558 °C
• PSA: 63.32000
• Density: 1.076 g/cm³
• LogP: 2.06900
• Storage Temp.: Store at 0°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

beta-Cyclohexyl-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)CC(C(=O)O)N
• Isomeric SMILES: C1CCC(CC1)C[C@@H](C(=O)O)N
• Description: L-Cyclohexylalanine is a kind of amino acid analog. It has some pharmacological effects. Study has shown that some of its derivatives exhibit potent bactericidal activity against drug-resistant gram-positive pathogens. Its derivatives can also act as dipeptidyl peptidase-IV inhibitor, which can be used for the treatment or prevention of diabetes.
• Uses: (S)-(+)-Cyclohexylalanine

Technology Process of (S)-2-amino-3-cyclohexylpropanoic acid

There total 40 articles about (S)-2-amino-3-cyclohexylpropanoic 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: 96.0%

N-(Benzyloxycarbonyl)-2(S)-amino-3-cyclohexylpropionic acid (119860-59-2) → β-cyclohexylalanine (4441-50-3,27527-05-5,55658-63-4,58717-02-5)

Guidance literature:

With cyclohexene; palladium on activated charcoal; In ethanol; for 0.333333h; Heating;

DOI:10.1039/a707067e

Reference yield: 61.0%

3-cyclohexyl-2-oxo-propionic acid (5962-91-4) → β-cyclohexylalanine (4441-50-3,27527-05-5,55658-63-4,58717-02-5)

Guidance literature:

With phenylglycin; In water; acetonitrile; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.8b03910

Reference yield:

cyclohexanepropionic acid (701-97-3) → L-cyclohexylalanine (27527-05-5) + 3-cyclohexyl-D-alanine (58717-02-5)

Guidance literature:

With C₁₉H₂₅N₃O*3ClH; acetic acid; 2,2-diphenylglycine; In ethanol; water; at 25 ℃; for 24h; Overall yield = 76 %; enantioselective reaction;

DOI:10.1016/j.tetlet.2018.01.089

upstream raw materials:

L-phenylalanine

(2S,4S)-4-(cyclohexylmethyl)-2-(1,1-dimethylethyl)-5-oxo-3-oxazolidinecarboxylic acid phenylmethyl ester

L-tyrosine

(S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid

Downstream raw materials:

morpholinocarbonylhexahydro-L-phenylalanine

methyl L-cyclohexylalaninate

(S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid

(S)-2-amino-3-cyclohexyl-propionic acid ethyl ester; hydrochloride

Refernces

• 1、 Rudman et al.. "-". . p. 551. Retrieved 1952.
• 2、 Gugkaeva, Zalina T.,Larionov, Vladimir A.,Maleev, Victor I.,Smol'yakov, Alexander F.. "A general asymmetric synthesis of artificial aliphatic and perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling reaction". supporting information. p. 5327 - 5332. Retrieved 2021/06/28.
• 3、 Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols". supporting information. p. 709 - 713. Retrieved 2019/01/25.