Viquidil

Base Information

• Chemical Name: Viquidil
• CAS No.: 84-55-9
• Molecular Formula: C20H24 N2 O2
• Molecular Weight: 324.423
• Hs Code.: 2933990090
• European Community (EC) Number: 201-540-1
• UNII: 48T4S8667S
• DSSTox Substance ID: DTXSID401016739
• Nikkaji Number: J4.897F
• Wikidata: Q27259181
• NCI Thesaurus Code: C152896
• Mol file: 84-55-9.mol

Synonyms:3-(3-ethenyl-4-piperidinyl)-1-(6-methoxy-4-quinolinyl)-1-propanone;Desclidium;LM 192;LM-192;viquidil;viquidil hydrochloride, (3R-trans)-isomer;viquidil monohydrochloride;viquidil monohydrochloride, (3R-trans)-isomer;viquidil, (3R-cis)-isomer

Chemical Property of Viquidil

Chemical Property:

• Vapor Pressure: 7.23E-10mmHg at 25°C
• Melting Point: 60°C
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 493.1°C at 760 mmHg
• Flash Point: 252°C
• PSA: 51.22000
• Density: 1.125g/cm³
• LogP: 3.94680
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 324.183778013
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

99%, ^*data from raw suppliers

1-(6-Methoxyquinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)propan-1-one 97% ^*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)CCC3CCNCC3C=C
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)C(=O)CC[C@@H]3CCNC[C@@H]3C=C
• Uses: 1-(6-Methoxyquinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)propan-1-one (CAS# 84-55-9) is in intermediate in the synthesis of Quinotoxine Hydrochloride (Q753500), an isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks. Vasodilator (cerebral).
• Therapeutic Function: Vasodilator, Antiarrhythmic

Technology Process of Viquidil

There total 29 articles about Viquidil 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: 75.0%

quinine (130-95-0) → viquidil (84-55-9)

Guidance literature:

With water; acetic acid; at 102 ℃; for 36h;

DOI:10.1002/anie.200705421

Reference yield: 66.0%

Quinine (130-95-0) → viquidil (84-55-9)

Guidance literature:

With acetic acid; at 102 ℃; for 72h;

Reference yield: 56.0%

quinine (130-95-0) → qunidine (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) + viquidil (84-55-9)

Guidance literature:

With acetic acid; In water; at 80 ℃; for 240h; Inert atmosphere;

DOI:10.1021/jm2002124

upstream raw materials:

6-methoxyquinoline-4-carboxylic acid ethyl ester

3-((4R)-1-benzoyl-3c-vinyl-[4r]piperidyl)-propionic acid ethyl ester

quinine; hydrogen sulfate dihydrate

rac-6'-methoxy-1,8-seco-cinchonan-9-one

Downstream raw materials:

L-Tartaric acid

6-methoxyquinoline-4-carboxylic acid

C₃₄H₄₁N₃O₅

C₂₇H₂₈N₂O₃

Refernces

• 1、 Ciardiello,Stewart,Sore,Galloway,Spring. "A novel complexity-to-diversity strategy for the diversity-oriented synthesis of structurally diverse and complex macrocycles from quinine". . p. 2825 - 2843. Retrieved 2017/05/29.
• 2、 Huigens III, Robert W.,Morrison, Karen C.,Hicklin, Robert W.,Flood J.r., Timothy A.,Richter, Michelle F.,Hergenrother, Paul J.. "A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products". . p. 195 - 202. Retrieved 2013/05/09.