Cotarnine

Base Information

• Chemical Name: Cotarnine
• CAS No.: 82-54-2
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• European Community (EC) Number: 201-429-8
• NSC Number: 121978
• UNII: 79V56TDI6G
• DSSTox Substance ID: DTXSID80274484,DTXSID40871559
• Nikkaji Number: J40.727E
• Wikidata: Q27266783
• NCI Thesaurus Code: C79913
• Metabolomics Workbench ID: 71487
• ChEMBL ID: CHEMBL4745550
• Mol file: 82-54-2.mol

Synonyms:cotarnine

Chemical Property of Cotarnine

Chemical Property:

• Melting Point: 132.5°C (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 365.3°Cat760mmHg
• PKA: 12.82±0.20(Predicted)
• Flash Point: 174.7°C
• PSA: 51.16000
• Density: 1.321g/cm³
• LogP: 0.84060
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 288

Purity/Quality:

99%, ^*data from raw suppliers

4-Methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C(=C2C1O)OC)OCO3
• Uses: Cotarnine is an intermediate in synthesizing Cotarnine Chloride (C717500), an oxidative degradation product of the drug Noscapine.

Technology Process of Cotarnine

There total 45 articles about Cotarnine 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: 91.0%

hydrocotarnine (550-10-7) → 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol (82-54-2)

Guidance literature:

With sodium hydroxide; iodine; In ethanol; water; potassium acetate;

Reference yield: 90.0%

1S,9R-(+)-α-narcotine (35933-64-3) → 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol (82-54-2)

Guidance literature:

With nitric acid; at 57 ℃; for 2h;

DOI:10.1002/chem.201603003

Reference yield: 90.0%

noscapine (128-62-1) → 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol (82-54-2)

Guidance literature:

noscapine; With nitric acid; at 25 - 57 ℃; for 2.08333h;

With potassium hydroxide;

DOI:10.1002/ejoc.201700471

upstream raw materials:

hydrocotarnine

(±)-α-noscapine

acetic acid

(-)-α-narcotinediol

Downstream raw materials:

(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-amine

2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-phenylethan-1-one

4-methoxy-6-methyl-5-(N'-phenyl-hydrazino)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

2-((Z)-4-methoxy-6-methyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-5-ylidene)-1-phenyl-ethanone

Refernces

• 1、 Rout, Laxmidhar,Parida, Bibhuti Bhusan,Phaomei, Ganngum,Emmanuel, Bertounesque,Sahoo, Akhila Kumar. "Synthesis of acyl derivatives of cotarnine". . p. 455 - 471. Retrieved 2019/08/20.
• 2、 Rout, Laxmidhar,Parida, Bibhuti Bhusan,Florent, Jean-Claude,Johannes, Ludger,Choudhury, Santosh Kumar,Phaomei, Ganngam,Scanlon, Joe,Bertounesque, Emmanuel. "Metal-Free Activation of a C(sp)?H Bond of Aryl Acetylenes". supporting information. p. 14812 - 14815. Retrieved 2016/10/11.