Corynoline

Base Information

• Chemical Name: Corynoline
• CAS No.: 18797-79-0
• Molecular Formula: C₂₁H₂₁NO₅
• Molecular Weight: 367.401
• Hs Code.: 29389090
• European Community (EC) Number: 683-177-2
• UNII: ZQ9W3JU6N3
• DSSTox Substance ID: DTXSID20940272
• Nikkaji Number: J34.215G
• Wikipedia: Corynoline
• Wikidata: Q15410919
• Metabolomics Workbench ID: 64048
• ChEMBL ID: CHEMBL4126384
• Mol file: 18797-79-0.mol

Synonyms:corynoline

Chemical Property of Corynoline

Chemical Property:

• Vapor Pressure: 5.48E-11mmHg at 25°C
• Melting Point: 217-218oC
• Refractive Index: 1.659
• Boiling Point: 504.201 °C at 760 mmHg
• PKA: 14.14±0.40(Predicted)
• Flash Point: 258.732 °C
• PSA: 60.39000
• Density: 1.396 g/cm³
• LogP: 2.44330
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 367.14197277
• Heavy Atom Count: 27
• Complexity: 603

Purity/Quality:

98% ^*data from raw suppliers

Corynoline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(CC3=CC4=C(C=C3C1N(CC5=C2C=CC6=C5OCO6)C)OCO4)O
• Isomeric SMILES: C[C@]12[C@H](CC3=CC4=C(C=C3[C@H]1N(CC5=C2C=CC6=C5OCO6)C)OCO4)O
• Description: The empirical formula of corynoline should read C21H21NO5
• Uses: Corynoline is an isoquinoline alkaloid with reported pharmacological activity such as cell adhesion inhibition, sedation and liver protection.

Technology Process of Corynoline

There total 20 articles about Corynoline 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: 53.0%

4bα,5,6,10b,11,12-hexahydro-5,10bα-dimethyl-2,3;7,8-bis(methylenedioxy)benzophenathridine-11α,12α-diol (55739-69-0,55781-75-4,61615-96-1,61615-97-2,70160-42-8,74708-05-7,74708-07-9) → (+/-)-11-epicorynoline (18797-79-0,51095-71-7,51151-82-7,68035-45-0,70191-84-3,74163-86-3,83607-66-3,83607-67-4,112438-07-0,114580-51-7)

Guidance literature:

With hydrogenchloride; perchloric acid; hydrogen; palladium on activated charcoal; at 50 ℃; for 24h; under 3800 Torr;

Reference yield: 53.0%

4bα,5,6,10b,11,12-hexahydro-5,10bα-dimethyl-2,3;7,8-bis(methylenedioxy)benzophenathridine-11α,12β-diol (55739-69-0,55781-75-4,61615-96-1,61615-97-2,70160-42-8,74708-05-7,74708-07-9) → (+/-)-11-epicorynoline (18797-79-0,51095-71-7,51151-82-7,68035-45-0,70191-84-3,74163-86-3,83607-66-3,83607-67-4,112438-07-0,114580-51-7)

Guidance literature:

With hydrogenchloride; perchloric acid; hydrogen; palladium on activated charcoal; at 50 ℃; for 24h; under 3800 Torr;

Reference yield:

3,4-dihydro-2-methyl-6,7-methylenedioxynaphthalen-1(2H)-one (1207-57-4) → (+/-)-11-epicorynoline (18797-79-0,51095-71-7,51151-82-7,68035-45-0,70191-84-3,74163-86-3,83607-66-3,83607-67-4,112438-07-0,114580-51-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) titanium tetrachloride, 2.) triethylamine / 1.) chloroform, reflux, 1 h, 2.) benzene, 2 h

2: 20 percent / methanol / 16 h / Ambient temperature; Irradiation

3: 21 percent / hydrogen / palladium-charcoal / methanol / 2 h / 50 °C / 1900 Torr

4: 28 percent / dichlorodicyanobenzoquinone / CHCl₃ / 24 h / 4 °C

5: 1.) performic acid, 2.) sodium hydroxide / 1.) formic acid, room temperature, 1 h, 2.) methanol, reflux, 2 h

6: 83 percent / lithium aluminium hydride

7: 53 percent / hydrogen, hydrochloric acid, perchloric acid / palladium-charcoal / 24 h / 50 °C / 3800 Torr

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; perchloric acid; Peroxyformic acid; hydrogen; titanium tetrachloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In methanol; chloroform;

upstream raw materials:

5b,13-dimethyl-(5br,12bc)-5b,12b,13,14-hexahydro-7H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-6-one

C₂₁H₂₀NO₅⁽¹⁺⁾

4bα,5,6,10b,11,12-hexahydro-5,10bα-dimethyl-2,3;7,8-bis(methylenedioxy)benzophenathridine-11α,12α-diol

4bα,5,6,10b,11,12-hexahydro-5,10bα-dimethyl-2,3;7,8-bis(methylenedioxy)benzophenathridine-11α,12β-diol

Downstream raw materials:

(+/-)-acetylcorynoline

(+)-corynoloxine

(+)-14-Epicorynolin-O-Acetat

acetylcorynoline

Refernces

• 1、 Ninomiya, Ichiya,Yamamoto, Okiko,Naito, Takeaki. "Photocyclisation of Enamides. Part 17. Total Synthesis of (+/-)-Corynoline, (+/-)-12-Hydroxycorynoline, and (+/-)-11-Epicorynoline". . p. 212 - 216. Retrieved 2007/10/02.