R-(-)-Flecainide

Base Information

• Chemical Name: R-(-)-Flecainide
• CAS No.: 99495-90-6
• Molecular Formula: C₁₇H₂₀F₆N₂O₃
• Molecular Weight: 414.348
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID80424962
• Nikkaji Number: J401.529K
• Wikidata: Q82237717
• ChEMBL ID: CHEMBL398673
• Mol file: 99495-90-6.mol

Synonyms:R-(-)-Flecainide;99495-90-6;(R)-Flecainide;N-[[(2R)-piperidin-2-yl]methyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide;R-Flecainide;R-()-Flecainide;K4D;Tocris-1470;Lopac-F-6777;SCHEMBL14971;CHEMBL398673;DTXSID80424962;DJBNUMBKLMJRSA-LLVKDONJSA-N;N-[(2R)-2-Piperidinylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide;NCGC00015443-01;NCGC00015443-02;NCGC00015443-03;NCGC00015443-09;NCGC00025175-01;'N-{[(2R)-piperidin-2-yl]methyl}-2,5-bis(2,2,2-trifluoroethoxy)benzamide'

Chemical Property of R-(-)-Flecainide

Chemical Property:

• Vapor Pressure: 9.11E-08mmHg at 25°C
• Refractive Index: 1.457
• Boiling Point: 434.9°C at 760 mmHg
• PKA: 14.15±0.46(Predicted)
• Flash Point: 216.8°C
• PSA: 59.59000
• Density: 1.286g/cm³
• LogP: 4.16040
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 414.13781148
• Heavy Atom Count: 28
• Complexity: 500

Purity/Quality:

95% ^*data from raw suppliers

R-(-)-Flecainide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
• Isomeric SMILES: C1CCN[C@H](C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
• Description: R-(–)-Flecainide is the (R) enantiomer of the antiarrhythmic agent flecainide . R-(–)-Flecainide prevents chloroform-induced ventricular fibrillation in mice (ED50 = 14.5 mg/kg). It also prevents ouabain-induced ectopic ventricular tachycardia in anesthetized dogs.
• Uses: R-Enantiomer of Flecainide. Antiarrhythmic (class IC) R-Enantiomer of Flecainide. Antiarrhythmic (class IC).

Technology Process of R-(-)-Flecainide

There total 3 articles about R-(-)-Flecainide 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:

flecainide (54143-55-4) → (+)-Flecainide (99495-92-8) + (-)-Flecainide (99495-90-6)

Guidance literature:

With Chirosil RCA(+); at 20 ℃; Resolution of racemate;

DOI:10.1002/chir.20818

Reference yield:

flecainide (54143-55-4) → (-)-flecainide (99495-90-6)

Guidance literature:

DOI:10.1021/jm00152a021

Reference yield:

N-(R)-1-Piperidin-2-ylmethyl-2,5-bis-(2,2,2-trifluoro-ethoxy)-benzamide; compound with (R)-hydroxy-phenyl-acetic acid → (-)-Flecainide (99495-90-6)

Guidance literature:

With sodium hydroxide; Yield given;

upstream raw materials:

flecainide

Refernces

• 1、 Lee, Areum,Choi, Hee Jung,Hyun, Myung Ho. "Liquid chromatographic direct resolution of flecainide and its analogs on a chiral stationary phase based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid". experimental part. p. 693 - 698. Retrieved 2010/09/16.