N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

Base Information

• Chemical Name: N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• CAS No.: 4423-58-9
• Molecular Formula: C11H14N2O5
• Molecular Weight: 254.243
• European Community (EC) Number: 225-030-3
• NSC Number: 63859
• Nikkaji Number: J89.938K
• Metabolomics Workbench ID: 147182
• Mol file: 4423-58-9.mol

Synonyms:corynecin I;N-acetyl-4-nitrophenylserinol;N-acetyl-4-nitrophenylserinol, (D-threo)-isomer;N-acetyl-4-nitrophenylserinol, (L-threo)-isomer;N-acetyl-p-nitrophenylserinol

Chemical Property of N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

Chemical Property:

• PSA: 115.38000
• LogP: 1.03930
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 254.09027155
• Heavy Atom Count: 18
• Complexity: 296

Purity/Quality:

98%min ^*data from raw suppliers

CorynecinI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CO)C(C1=CC=C(C=C1)[N+](=O)[O-])O
• Isomeric SMILES: CC(=O)N[C@H](CO)[C@@H](C1=CC=C(C=C1)[N+](=O)[O-])O
• Description: Corynecin I is a chloramphenicol-like antibiotic originally isolated from Corynebacterium. It is active against Gram-positive and Gram-negative bacteria with MIC values of 5.2-83 μg/ml for S. sonnei, P. vulgaris, K. pneumoniae, and S. aureus among others.
• Uses: Corynecin I is a member of a naturally-occurring complex of chloramphenicol-like acyl nitrophenylpropylamines isolated from Corynebacterium hydrocarboclastus in 1972. Corynecin I is active against Gram positive and Gram negative bacteria. Although less potent than chloramphenicol, corynecin I shows a similar species selectivity.

Technology Process of N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

There total 68 articles about N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide 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:

N-[1-hydroxymethyl-2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide (3123-13-5) → (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol (1885-08-1,4423-58-9,4618-99-9,15376-53-1,19934-66-8,112244-26-5,119364-49-7,119364-51-1) + (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol (1885-08-1,4423-58-9,4618-99-9,15376-53-1,19934-66-8,112244-26-5,119364-49-7,119364-51-1)

Guidance literature:

With sodium tetrahydroborate; ethanol;

Reference yield:

N-[1-hydroxymethyl-2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide (3123-13-5) → (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol (1885-08-1,4423-58-9,4618-99-9,15376-53-1,19934-66-8,112244-26-5,119364-49-7,119364-51-1) + (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol (1885-08-1,4423-58-9,4618-99-9,15376-53-1,19934-66-8,112244-26-5,119364-49-7,119364-51-1)

Guidance literature:

With sodium tetrahydroborate; ethanol;

Reference yield:

(1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane (33485-02-8,51259-82-6,92870-92-3) → (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol (1885-08-1,4423-58-9,4618-99-9,15376-53-1,19934-66-8,112244-26-5,119364-49-7,119364-51-1)

Guidance literature:

With sodium hydroxide; acetone;

DOI:10.1021/ja01175a066

upstream raw materials:

(1S)-10-camphorsulfonic acid

(1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol

(1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

Downstream raw materials:

threo-(1S,2S)-2-acetamino-1-(4-nitrophenyl)-1,3-propanediol

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

(1R,2R)-2-acetylamino-1-(4-dimethylamino-phenyl)-propane-1,3-diol

N-[(1RS,2RS)-2-(4-amino-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-acetamide

Refernces

• 1、 Wang, Xu,Wang, Yun-Xia,Yuan, Baoling,Cui, Hao-Jie,Fu, Ming-Lai. "Fabrication of resin supported Au-Pd bimetallic nanoparticle composite to efficiently remove chloramphenicol from water". . p. 18806 - 18812. Retrieved 2015/04/22.
• 2、 Fujii, Ikuo,Tanaka, Fujie,Miyashita, Hideaki,Tanimura, Ryuji,Kinoshita, Keiko. "Correlation between antigen-combining-site structures and functions within a panel of catalytic antibodies generated against a single transition state analog". . p. 6199 - 6209. Retrieved 2007/10/02.