Cinchonan-9-one, 6'-methoxy-, (8alpha)-

Base Information

• Chemical Name: Cinchonan-9-one, 6'-methoxy-, (8alpha)-
• CAS No.: 84-31-1
• Molecular Formula: C20H22 N2 O2
• Molecular Weight: 322.407
• Hs Code.: 2939200050
• European Community (EC) Number: 201-524-4
• UNII: 956671AJG7
• DSSTox Substance ID: DTXSID70871567
• Wikidata: Q27271744
• Mol file: 84-31-1.mol

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

Chemical Property of Cinchonan-9-one, 6'-methoxy-, (8alpha)-

Chemical Property:

• Vapor Pressure: 2.72E-09mmHg at 25°C
• Melting Point: 108° (rapid heating)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 477.8°C at 760 mmHg
• Flash Point: 242.8°C
• PSA: 42.43000
• Density: 1.21g/cm³
• LogP: 3.26040
• Water Solubility.: 3mg/L(20 oC)
• 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% ^*data from raw suppliers

Quininone ^*data from reagent 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
• Uses: Quininone has been shown to have antimalarial activity in mice. Quininone has been shown to aid the binding of drug-induced antibodies to human platelets.

Technology Process of Cinchonan-9-one, 6'-methoxy-, (8alpha)-

There total 13 articles about Cinchonan-9-one, 6'-methoxy-, (8alpha)- 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: 100.0%

quinine (130-95-0) → quininone (84-31-1)

Guidance literature:

With benzophenone; potassium tert-butylate; In toluene; for 6h; Heating;

DOI:10.1016/S0040-4039(01)00404-X

Reference yield: 96.0%

Quinine (130-95-0) → 6'-methoxycinchonidone (84-31-1)

Guidance literature:

With benzophenone; potassium tert-butylate; In toluene; for 16h; Inert atmosphere; Reflux;

DOI:10.1021/ja9100276

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

upstream raw materials:

9-epiquinine

acetic acid

quinidine

Quinine

Downstream raw materials:

quinine

quinine

6-methoxyquinoline-4-carboxylic acid

isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate

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、 -. "VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE". Paragraph 0078; 0079; 0080; 0081; 0082. . Retrieved 2013/11/19.