Quinidinone

Base Information

• Chemical Name: Quinidinone
• CAS No.: 14528-53-1
• Deprecated CAS: 300664-47-5
• Molecular Formula: C20H22 N2 O2
• Molecular Weight: 322.407
• Hs Code.: 2933990090
• European Community (EC) Number: 238-549-5
• DSSTox Substance ID: DTXSID301021294
• Wikidata: Q110185023
• Metabolomics Workbench ID: 155899
• ChEMBL ID: CHEMBL2262642
• Mol file: 14528-53-1.mol

Synonyms:6'-methoxycinchonan-9-one;quininone;quininone, (8alpha)-isomer

Chemical Property of Quinidinone

Chemical Property:

• Boiling Point: 477.8°Cat760mmHg
• PKA: 7.45±0.70(Predicted)
• Flash Point: 242.8°C
• PSA: 42.43000
• Density: 1.21g/cm³
• LogP: 3.26040
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 494

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(=O)C3CC4CCN3CC4C=C
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)C(=O)[C@H]3C[C@@H]4CCN3C[C@@H]4C=C

Technology Process of Quinidinone

There total 12 articles about Quinidinone 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: 80.0%

(6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → (6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanone (84-31-1,14528-53-1,72402-46-1,72402-47-2,101143-89-9,101143-92-4,146925-11-3)

Guidance literature:

With barium permanganate; In acetonitrile; for 2h; Heating;

DOI:10.1055/s-1989-27256

Reference yield: 61.0%

Quinine (130-95-0) → 6'-methoxycinchoninone (14528-53-1)

Guidance literature:

With potassium iodide; In water; acetonitrile; at 20 ℃; electrochemical oxidation (on platinum electrodes , pot. 0.9-1.1 V);

Reference yield:

9-epiquinine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → 6'-methoxycinchonidone (84-31-1) + 6'-methoxycinchoninone (14528-53-1)

Guidance literature:

With water; acetic acid; dihydrogen peroxide; at 70 - 80 ℃;

DOI:10.1016/S0040-4020(01)90029-8

upstream raw materials:

benzophenone

Quinine

9-fluorenone

quinine

Downstream raw materials:

9-epiquinine

quinidine

Quinine

quinine

Refernces

• 1、 Trenti, Francesco,Yamamoto, Kotaro,Hong, Benke,Paetz, Christian,Nakamura, Yoko,O'Connor, Sarah E.. "Early and Late Steps of Quinine Biosynthesis". supporting information. p. 1793 - 1797. Retrieved 2021/04/05.
• 2、 Boratynski, Przemyslaw J.,Turowska-Tyrk, Ilona,Skarzewski, Jacek. "Synthetic approaches to 9-arylated Cinchona alkaloids: Stereoselective addition of Grignard reagents to cinchonanones and hydroxylation of 9-phenylcinchonanes". scheme or table. p. 876 - 883. Retrieved 2012/09/21.