L-Phenylalanine-cyclohexylamide

Base Information

• Chemical Name: L-Phenylalanine-cyclohexylamide
• CAS No.: 17186-53-7
• Molecular Formula: C₁₅H₂₂N₂O
• Molecular Weight: 246.352
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00350936
• Nikkaji Number: J656.280I
• Wikidata: Q82127006
• Mol file: 17186-53-7.mol

Synonyms:17186-53-7;H-PHE-CYCLOHEXYLAMIDE;L-Phenylalanine-cyclohexylamide;N-Cyclohexyl-L-phenylalaninamide;(2S)-2-amino-N-cyclohexyl-3-phenylpropanamide;(S)-2-amino-N-cyclohexyl-3-phenylpropanamide;L-Phenylalanine cyclohexylamide;SCHEMBL353959;DTXSID00350936;ZMBVNXGMRQPTHV-AWEZNQCLSA-N;MFCD00672357;AS-46842;CS-0333883;F10691;J-010773

Chemical Property of L-Phenylalanine-cyclohexylamide

Chemical Property:

• Melting Point: 96-99 °C
• PSA: 55.12000
• LogP: 3.09650
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 246.173213330
• Heavy Atom Count: 18
• Complexity: 255

Purity/Quality:

95% ^*data from raw suppliers

N-Cyclohexyl-L-phenylalaninamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)NC(=O)C(CC2=CC=CC=C2)N
• Isomeric SMILES: C1CCC(CC1)NC(=O)[C@H](CC2=CC=CC=C2)N

Technology Process of L-Phenylalanine-cyclohexylamide

There total 17 articles about L-Phenylalanine-cyclohexylamide 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: 95.2%

N-tert-butyloxycarbonyl-(L)-phenylalanine cyclohexylamide (169566-77-2) → L-phenylalanine cyclohexylamide (17186-53-7,92698-80-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/hlca.19950780305

Reference yield: 82.0%

N-<(S)-1-<(S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl>-3-isobutyl-2,5-dioxo-pyrrolidin-3-yl>-benzamide → L-phenylalanine cyclohexylamide (17186-53-7,92698-80-1) + (S)-N-(1-amino-3-isobutyl-2,5-dioxo-pyrrolidin-3-yl)-benzamide

Guidance literature:

With hydrazine hydrate; In ethanol; for 18h; Heating;

DOI:10.1016/0040-4020(95)00665-U

Reference yield: 81.0%

N-<(R)-1-<(S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl>-3-methyl-2,5-dioxo-pyrrolidin-3-yl>-benzamide → L-phenylalanine cyclohexylamide (17186-53-7,92698-80-1) + (R)-N-(1-amino-3-methyl-2,5-dioxo-pyrrolidin-3-yl)-benzamide

Guidance literature:

With hydrazine hydrate; In ethanol; for 18h; Heating;

DOI:10.1016/0040-4020(95)00665-U

upstream raw materials:

Cbz-L-Phe-cyclohexylNH

acetic acid

N-tert-butyloxycarbonyl-(L)-phenylalanine cyclohexylamide

N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester

Downstream raw materials:

N²-<(R)-N²-benzoyl-2-methyl-phenylalanyl>-(S)-phenylalanine cyclohexylamide

(1S,2S)-[1-benzamide-2-phenylcyclohexane-1-carboxamide]-(S)-phenylalanine cyclohexylamide

(1R,2R)-[1-benzamide-2-phenylcyclohexane-1-carboxamide]-(S)-phenylalanine cyclohexylamide

(S)-tert-butyl (4-((2-((1-(cyclohexylamino)-1-oxo-3-phenylpropan-2-yl)amino)-2-oxoethyl)amino)-4-oxobutyl)carbamate

Refernces

• 1、 Sabatini, Marco T.,Karaluka, Valerija,Lanigan, Rachel M.,Boulton, Lee T.,Badland, Matthew,Sheppard, Tom D.. "Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts". supporting information. p. 7033 - 7043. Retrieved 2018/05/04.
• 2、 Li, Jiuyuan,Luo, Sanzhong,Cheng, Jin-Pei. "Chiral primary-tertiary diamine catalysts derived from natural amino acids for syn-aldol reactions of hydroxy ketones". supporting information; experimental part. p. 1747 - 1750. Retrieved 2009/08/07.