4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile

Base Information

• Chemical Name: 4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile
• CAS No.: 156732-12-6
• Molecular Formula: C25H24 N2 O
• Molecular Weight: 368.478
• DSSTox Substance ID: DTXSID90433262
• Nikkaji Number: J623.092J
• Wikidata: Q72463576
• Mol file: 156732-12-6.mol

Synonyms:156732-12-6;4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile;4S-4-Dibenzylamino-3-oxo-5-phenylpentanonitrile;(4S)-4-(DIBENZYLAMINO)-3-OXO-5-PHENYLPENTANENITRILE;4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile;Benzenepentanenitrile, gamma-[bis(phenylmethyl)amino]-beta-oxo-, (gammaS)-;SCHEMBL2059348;DTXSID90433262;MYTIELGBBUTMMA-DEOSSOPVSA-N;AKOS015914673;CS-0130715;(S)-3-Oxo-4-dibenzylamino-5-phenylpentanenitrile;(S)-4-(Dibenzylamino)-3-oxo-5-phenylpentanenitrile;J-009337;(4S)-4-(N,N-Dibenzylamino)-3-oxo-5-phenyl-pentanonitrile

Chemical Property of 4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile

Chemical Property:

• Boiling Point: 510.0±50.0 °C(Predicted)
• PKA: 8.71±0.10(Predicted)
• PSA: 44.10000
• Density: 1.136±0.06 g/cm3(Predicted)
• LogP: 4.78288
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 368.188863393
• Heavy Atom Count: 28
• Complexity: 484

Purity/Quality:

98%Min ^*data from raw suppliers

4S-4-Dibenzylamino-3-oxo-5-phenylpentanonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)CC#N)N(CC2=CC=CC=C2)CC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)CC#N)N(CC2=CC=CC=C2)CC3=CC=CC=C3
• Uses: An intermediate in the synthesis of Ritonavir.

Technology Process of 4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile

There total 5 articles about 4S-4-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile 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: 82.0%

N,N-dibenzyl-L-phenylalanine benzyl ester (111138-83-1) + acetonitrile (75-05-8,26809-02-9) → (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile (156732-12-6)

Guidance literature:

acetonitrile; With sodium amide; In tetrahydrofuran; at -45 ℃; for 0.5h; Inert atmosphere;

N,N-dibenzyl-L-phenylalanine benzyl ester; In tetrahydrofuran; at -45 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2018.10.001

Reference yield: 59.0%

→ (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile (156732-12-6)

Guidance literature:

Reference yield:

→ lithium diethylamide (816-43-3) + (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile (156732-12-6)

Guidance literature:

upstream raw materials:

N,N-dibenzyl-L-phenylalanine benzyl ester

acetonitrile

L-phenylalanine

Downstream raw materials:

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1-phenyl-6-methylheptane

(2S,3S,5S)-2-amino-5-[N-tert-butyloxycarbonylamino]-3-hydroxy-7-methyl-1-phenyloctane

((1S,3S,4S)-4-Amino-1-butyl-3-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester

[(1S,3S,4S)-4-Amino-3-hydroxy-1-(3-methyl-butyl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Matralis, Alexios N.,Xanthopoulos, Dimitrios,Huot, Geneviève,Lopes-Paciencia, Stéphane,Cole, Charles,de Vries, Hugo,Ferbeyre, Gerardo,Tsantrizos, Youla S.. "Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration". supporting information. p. 5547 - 5554. Retrieved 2018/10/15.
• 2、 Hongmin, Li,Bin, Wang,Shuyong, Mu. "Synthesis of (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one". . p. 1154 - 1156. Retrieved 2015/09/28.