Epiquinine

Base Information

• Chemical Name: Epiquinine
• CAS No.: 72402-51-8
• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.423
• European Community (EC) Number: 209-341-1
• UNII: 4M9989F55E
• DSSTox Substance ID: DTXSID601269906
• Wikidata: Q27166581
• Mol file: 72402-51-8.mol

Synonyms:Epiquinine;9-Epiquinine;572-60-1;UNII-4M9989F55E;EINECS 209-341-1;4M9989F55E;(S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol;(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;Conchinin;Quinidex;quinidin-;Chinidin [German];9-epi Quinine;4-[(S)-[(2S,4R,5R)-5-Vinyl-1-azabicyclo[2.2.2]octane-2-yl]hydroxymethyl]-6-methoxyquinoline;C20H24N2O2;Epichinin;NCI-C56246;(8-alpha,9S)-6'-Methoxycinchonan-9-ol;EPIQUININE [MI];SCHEMBL454393;Epiquinine, analytical standard;AMY383;CHEBI:94816;DTXSID601269906;PD070333;C90149;Cinchonan-9-ol, 6'-methoxy-, (8alpha,9S)-;EN300-366944;BRD-K99257182-311-01-4;Q27166581;CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9S)-;Cinchonan-9-ol, 6'-methoxy-, (8alpha,9S)-(+/-)-;(S)-[(2S,4S,5R)-5-ETHENYL-1-AZABICYCLO[2.2.2]OCTAN-2-YL](6-METHOXYQUINOLIN-4-YL)METHANOL;72402-51-8

Chemical Property of Epiquinine

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 324.183778013
• Heavy Atom Count: 24
• Complexity: 457

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Epiquinine

There total 107 articles about Epiquinine 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: 95.0%

quinidine acetate (56652-53-0) → quinindine (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)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.066

Reference yield: 75.0%

(3R,4S)-4-[(2S,3S)-3-(6-Methoxy-quinolin-4-yl)-oxiranylmethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (865853-19-6) → quinindine (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)

Guidance literature:

With cesium fluoride;

DOI:10.1016/j.tetlet.2005.06.171

Reference yield:

6-Methoxy-4-[(2S,3S)-3-((3R,4S)-3-vinyl-piperidin-4-ylmethyl)-oxiranyl]-quinoline → quinindine (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)

Guidance literature:

In acetonitrile; at 185 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1021/ja039550y

upstream raw materials:

quinidine

Quinine

O-tosylquinine

water

Downstream raw materials:

6'-methoxycinchonidone

6'-methoxycinchoninone

viquidil

Quinine