(-)-N-Formylcytisine

Base Information

• Chemical Name: (-)-N-Formylcytisine
• CAS No.: 53007-06-0
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25
• UNII: 4VKB5IP54F
• DSSTox Substance ID: DTXSID00967487
• Nikkaji Number: J445.373E
• Wikidata: Q27260566
• Mol file: 53007-06-0.mol

Synonyms:N-Formylcytisine;(-)-N-Formylcytisine;53007-06-0;N-Formylcytisine, (-)-;(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-diene-11-carbaldehyde;(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.0?,?]trideca-2,4-diene-11-carbaldehyde;1,5-Methano-2H-pyrido(1,2-a)(1,5)diazocine-3(4H)-carboxaldehyde, 1,5,6,8-tetrahydro-8-oxo-, (1R,5S)-;DTXSID00967487;HY-N7625;6-oxo-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-diene-11-carbaldehyde;AKOS024282716;MS-23204;CS-0134817;Q27260566;8-Oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocine-3(4H)-carbaldehyde

Chemical Property of (-)-N-Formylcytisine

Chemical Property:

• Vapor Pressure: 1.25E-10mmHg at 25°C
• Boiling Point: 512.8°C at 760 mmHg
• PKA: 0.00±0.20(Predicted)
• Flash Point: 267.4°C
• PSA: 42.31000
• Density: 1.31g/cm³
• LogP: 0.99760
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 400

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

N-Formylcytisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CN(CC1C3=CC=CC(=O)N3C2)C=O
• Isomeric SMILES: C1[C@H]2CN(C[C@@H]1C3=CC=CC(=O)N3C2)C=O
• Description: This derivative of cytisine has recently been isolated from Thermopsis chinensis. It yields colourless needles from CH2Cl2-Et20 and is laevorotatory having a specific rotation of [α]20 D- 233° (c 0.5, EtOH). It gives an ultraviolet spectrum in EtOH having absorption maxima at 232 and 309 nm.
• Uses: N-Formylcytisine is a derivative of Cytisine (C998500) that can be used as a ligand for neuronal nicotine receptors.

Technology Process of (-)-N-Formylcytisine

There total 7 articles about (-)-N-Formylcytisine 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: 96.0%

cytisine (485-35-8) + formic acid ethyl ester (109-94-4) → N-formylcytisine (53007-06-0)

Guidance literature:

With triethylamine; for 19h; Reflux;

DOI:10.1002/anie.201712852

Reference yield: 95.0%

formic acid (64-18-6) + cytisine (485-35-8) → N-formylcytisine (53007-06-0)

Guidance literature:

With acetic acid; for 2h; Heating;

DOI:10.1023/A:1013778703658

Reference yield: 79.0%

formyl acetic anhydride (2258-42-6) + cytisine (485-35-8) → N-formylcytisine (53007-06-0)

Guidance literature:

In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201501627

upstream raw materials:

formic acid

cytisine

formyl acetic anhydride

formic acid ethyl ester

Refernces

• 1、 Scharnagel, Dagmar,Goller, Jessica,Deibl, Nicklas,Milius, Wolfgang,Breuning, Matthias. "The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach". . p. 2432 - 2435. Retrieved 2018/02/16.