D-Cyclohexylglycine

Base Information

• Chemical Name: D-Cyclohexylglycine
• CAS No.: 14328-52-0
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.213
• Hs Code.: 29224999
• UNII: KU105BHB7U
• DSSTox Substance ID: DTXSID50353119
• Nikkaji Number: J58.540H
• Mol file: 14328-52-0.mol

Synonyms:D-Cyclohexylglycine;14328-52-0;h-d-chg-oh;(r)-2-amino-2-cyclohexylacetic acid;D-alpha-Cyclohexylglycine;(2R)-2-amino-2-cyclohexylacetic acid;2-Cyclohexyl-D-glycine;Cyclohexylglycine, (R)-;Cyclohexylglycine, (-)-;KU105BHB7U;D-2-CYCLOHEXYLGLYCINE;Cyclohexaneacetic acid, .alpha.-amino-, (.alpha.R)-;(2r)-amino(cyclohexyl)acetic acid;MFCD01311678;D-|A-Aminocyclohexylacetic Acid;d-a-cyclohexylglycine;UNII-KU105BHB7U;D-.alpha.-Cyclohexylglycine;SCHEMBL418060;(R)-2-CYCLOHEXYLGLYCINE;(R)-a-Aminocyclohexylacetic acid;DTXSID50353119;D-alpha-Aminocyclohexylacetic acid;D-alpha-Aminocyclohexaneacetic acid;CS-D1762;(R)-alpha-Aminocyclohexylacetic acid;AKOS016842454;(2r)-2-amino-2-cyclohexylethanoic acid;AC-24105;AS-17493;HY-42354;C2673;D-.ALPHA.-AMINOCYCLOHEXANEACETIC ACID;EN300-67363;D-alpha-Cyclohexylglycine, >=98.0% (HPLC);Cyclohexaneacetic acid, alpha-amino-, (alphaR)-;A808053;J-007789

Chemical Property of D-Cyclohexylglycine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.000441mmHg at 25°C
• Melting Point: 256 °C
• Refractive Index: 1.51
• Boiling Point: 292.8 °C at 760 mmHg
• PKA: 2.44±0.10(Predicted)
• Flash Point: 130.9 °C
• PSA: 63.32000
• Density: 1.12 g/cm³
• LogP: 1.67890
• Storage Temp.: 2-8°C
• Solubility.: DMSO
• Water Solubility.: Soluble
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 157.110278721
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

D-Cyclohexylglycine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C(=O)O)N
• Isomeric SMILES: C1CCC(CC1)[C@H](C(=O)O)N
• Description: D-alpha-Cyclohexylglycine is a kind of non-proteinogenic amino acid. It is widely presented in various natural products and pharmaceutical intermediates. It can be incorporated into the peptide inhibitors renders resistance from peptidases and proteinases and thereby imparts pharmacological stability to molecules. Some derivatives of Cyclohexylglycine has been recently been developed into inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes.
• Uses: D-Cyclohexylglycine (cas# 14328-52-0) is a compound useful in organic synthesis.

Technology Process of D-Cyclohexylglycine

There total 8 articles about D-Cyclohexylglycine 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: 95.8%

(R)-phenylglycine (875-74-1) → (R)-2-amino-2-cyclohexyl acetic acid (14328-52-0)

Guidance literature:

With hydrogenchloride; hydrogen; In water; isopropyl alcohol; at 50 - 60 ℃; for 6 - 8h;

Reference yield:

(R)-phenylglycine, N-salicylidene derivative (63546-36-1) → (R)-2-amino-2-cyclohexyl acetic acid (14328-52-0)

Guidance literature:

With hydrogen; platinum(IV) oxide;

DOI:10.1021/ja00365a098

Reference yield:

ristomycinic acid (54750-25-3) → (R)-2-amino-2-cyclohexyl acetic acid (14328-52-0) + (S)-Amino-(3,5-dihydroxy-4-methyl-phenyl)-acetic acid (76249-99-5)

Guidance literature:

With hydrogen;

DOI:10.1021/ja00365a098

upstream raw materials:

(R)-phenylglycine

(R)-benzoylamino-cyclohexyl-acetic acid

(S)-2-phenylglycine

(R)-(acetylamino)-(cyclohexyl)acetic acid

Downstream raw materials:

(2R)-cyclohexyl glycine ethyl ester

(R)-amino(cyclohexyl)acetic acid methyl ester

(R)-benzamino-cyclohexyl-acetic acid methyl ester

N-Tosyl-S-benzyl-cysteinyl-tyrosyl-(D-2-cyclohexyl-2-amino-essigsaeuremethylester)

Refernces

• 1、 Devant, Ralf,Braun, Manfred. "Stereoselective Aldol Reaction with Chiral Secondary Acetamides". . p. 2191 - 2207. Retrieved 2007/10/02.
• 2、 Harris, Constance M.,Harris, Thomas M.. "Structure of Ristocetin A: Configurational Studies of the Peptide". . p. 363 - 365. Retrieved 2007/10/02.