N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide

Base Information

• Chemical Name: N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide
• CAS No.: 4021-23-2
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• UNII: Q3J2K752LX
• DSSTox Substance ID: DTXSID70352366
• Wikidata: Q82129465
• Pharos Ligand ID: HDHM23VFBK5U
• ChEMBL ID: CHEMBL472080
• Mol file: 4021-23-2.mol

Synonyms:N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide;4021-23-2;2H-1-Benzopyran-3-carboxamide, N-cyclohexyl-2-oxo-;Q3J2K752LX;N-Cyclohexyl-2-oxo-2H-1-benzopyran-3-carboxamide;UNII-Q3J2K752LX;N-Cyclohexyl-2-oxidanylidene-chromene-3-carboxamide;N-cyclohexyl-2-oxochromene-3-carboxamide;ChemDiv2_003298;3-carboxamido coumarin, 1;Oprea1_254332;Oprea1_273725;CHEMBL472080;BDBM29152;DTXSID70352366;HMS1378F20;CCG-15837;STK408165;AKOS000533315;CL-426250;EU-0035943;EN300-26868413;SR-01000410421;SR-01000410421-1;Z31484706

Chemical Property of N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 271.12084340
• Heavy Atom Count: 20
• Complexity: 423

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)NC(=O)C2=CC3=CC=CC=C3OC2=O

Technology Process of N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide

There total 4 articles about N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide 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: 88.0%

2-oxo-2H-chromene-3-carboxylic acid (531-81-7) + cyclohexylamine (108-91-8,157973-60-9) → 2-oxo-2H-chromene-3-carboxylic acid cyclohexylamide (4021-23-2)

Guidance literature:

2-oxo-2H-chromene-3-carboxylic acid; With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;

cyclohexylamine; With dmap; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bioorg.2020.103700

Reference yield: 82.0%

cyclohexylamine (108-91-8,157973-60-9) + salicylaldehyde (90-02-8) + diethyl malonate (105-53-3) → 2-oxo-2H-chromene-3-carboxylic acid cyclohexylamide (4021-23-2)

Guidance literature:

With Ni-NiO nanoparticles; In ethanol; for 4h; Reflux; Green chemistry;

DOI:10.1039/c5ra13932e

Reference yield:

salicylaldehyde (90-02-8) → 2-oxo-2H-chromene-3-carboxylic acid cyclohexylamide (4021-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / water / 20 °C

2: N-ethyl-N,N-diisopropylamine; propyl phosphoric acid anhydride / N,N-dimethyl-formamide / 0.67 h / 0 °C

With propyl phosphoric acid anhydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.fitote.2018.03.013

upstream raw materials:

N-cyclohexyl-2-imino-2H-chromene-3-carboxamide

cyclohexylamine

salicylaldehyde

diethyl malonate

Refernces

• 1、 Yu, Xiang,Teng, Peng,Zhang, Ya-Ling,Xu, Zhao-Jun,Zhang, Ming-Zhi,Zhang, Wei-Hua. "Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives". . p. 387 - 395. Retrieved 2018/04/19.
• 2、 Helal, Mohamed H.,El-Hag Ali, Gameel A. M.,Ali, Ahmed A.,Ammar, Yousry A.. "One-step synthesis of chromene-3-carboxamide, bis-chromene, chromeno[3,4-c]pyridine and bischromeno[3,4-c]pyridine derivatives for antimicrobial evaluation". experimental part. p. 465 - 469. Retrieved 2011/01/12.