3H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-oxo-, ethyl ester

Base Information

• Chemical Name: 3H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-oxo-, ethyl ester
• CAS No.: 734-88-3
• Deprecated CAS: 134192-26-0
• Molecular Formula: C16H12 O4
• Molecular Weight: 268.269
• European Community (EC) Number: 211-997-9
• UNII: 5R5Q753KF5
• DSSTox Substance ID: DTXSID7061065
• Nikkaji Number: J193.104K
• Wikidata: Q81989296
• ChEMBL ID: CHEMBL1611632
• Mol file: 734-88-3.mol

Synonyms:5,6-benzocoumarin-3-carboxylic acid ethyl ester;ethyl 5,6-benzocoumarin-3-carboxylate

Chemical Property of 3H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-oxo-, ethyl ester

Chemical Property:

• Vapor Pressure: 4.06E-09mmHg at 25°C
• Refractive Index: 1.4872 (estimate)
• Boiling Point: 473°C at 760 mmHg
• Flash Point: 247.9°C
• PSA: 56.51000
• Density: 1.319g/cm³
• LogP: 3.12290
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 268.07355886
• Heavy Atom Count: 20
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=CC3=CC=CC=C32)OC1=O

Technology Process of 3H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-oxo-, ethyl ester

There total 35 articles about 3H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-oxo-, ethyl ester 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: 97.0%

2-hydroxynaphthalene-1-carbaldehyde (708-06-5) + diethyl malonate (105-53-3) → ethyl 5,6-benzocoumarin-3-carboxylate (734-88-3)

Guidance literature:

With piperidine; at 20 ℃; for 0.0833333h;

DOI:10.1246/cl.2001.110

Reference yield: 92.0%

ethyl 2-cyanoacetate (105-56-6) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → ethyl 5,6-benzocoumarin-3-carboxylate (734-88-3)

Guidance literature:

With iron(III) chloride; In ethanol; at 80 ℃; for 24h; Mechanism;

DOI:10.1080/00397911.2013.862833

Reference yield: 92.0%

→ ethyl 5,6-benzocoumarin-3-carboxylate (734-88-3)

Guidance literature:

With iron(III) chloride; at 80 ℃; for 6h;

upstream raw materials:

ethyl 3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carboxylate

2-hydroxynaphthalene-1-carbaldehyde

diethyl malonate

ethyl 2-cyanoacetate

Downstream raw materials:

3-oxo-3H-naphtho[2,1-b]pyran-2-carboxylic acid methyl ester

5,6-benzocoumarin-3N-(4'-(N'-4,6-dimethyl-pyrimimidyl-2)sulphonamidophenyl)carboxamide

5,6-benzocoumarin-3N-(4'-(N'-p-methylphenyl)sulphonamidophenyl)carboxamide

2-benzoyl-3(H)-hydroxy-3-phenylnaphtho<2,1-b>pyran

Refernces

• 1、 Ali, Mahammad,Dutta, Ananya,Islam, Abu Saleh Musha,Katarkar, Atul,Maiti, Debjani,Sasmal, Mihir. "A coumarin embedded highly sensitive nitric oxide fluorescent sensor: Kinetic assay and bio-imaging applications". . p. 8450 - 8458. Retrieved 2020.
• 2、 Abdul-Ridha, Nabeel A.,Salmaan, Afraah D.,Sabah, Rita,Saeed, Bahjat,Al-Masoudi, Najim A.. "Synthesis, cytotoxicity and in silico study of some novel benzocoumarin-chalcone-bearing aryl ester derivatives and benzocoumarin-derived arylamide analogs". . p. 201 - 210. Retrieved 2021/04/26.
• 3、 Chen, Guzhou,Liu, Peng-Yu,Zou, Huanhuan,Hu, Jiadong,Fang, Xiaowu,Xu, Dongyang,He, Yu-Peng,Wei, Hongbo,Xie, Weiqing. "Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole". supporting information. p. 2279 - 2284. Retrieved 2021/04/05.