Fawcettidine

Base Information

• Chemical Name: Fawcettidine
• CAS No.: 14912-31-3
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.365
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30331839
• Nikkaji Number: J34.221A
• Wikidata: Q5856916
• Metabolomics Workbench ID: 69326
• Mol file: 14912-31-3.mol

Synonyms:fawcettidine;fawcettimine

Chemical Property of Fawcettidine

Chemical Property:

• Vapor Pressure: 7.75E-07mmHg at 25°C
• Boiling Point: 407.1°Cat760mmHg
• PKA: 8.42±0.40(Predicted)
• Flash Point: 159.5°C
• PSA: 20.31000
• Density: 1.13g/cm³
• LogP: 2.92920
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 245.177964357
• Heavy Atom Count: 18
• Complexity: 427

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2CC(=O)C3C24CCCN(C4=C1)CCC3
• Isomeric SMILES: C[C@@H]1C[C@H]2CC(=O)[C@@H]3[C@]24CCCN(C4=C1)CCC3

Technology Process of Fawcettidine

There total 42 articles about Fawcettidine 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%

(2R,4aS,12aS)-2-methyl-2,3,6,7,9,10,12,12a-decahydro-4H,5H-benzo[e]pyrrole[3,2,1-ij]quinoline-4,11(1H)-dione (14478-54-7) → (+)-fawcettidine (14912-31-3)

Guidance literature:

With acetic acid; zinc; at 140 ℃; for 8h; Inert atmosphere;

DOI:10.1002/anie.201106753

Reference yield: 87.0%

(+)-lycoposerramine Q (481048-37-7) → (+)-fawcettidine (14912-31-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2014.11.041

Reference yield: 60.0%

C18H27NO2 (1042150-29-7) → (+)-fawcettidine (14912-31-3)

Guidance literature:

C₁₈H₂₇NO₂; With hydrogenchloride; water; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/anie.200800522

upstream raw materials:

C₁₈H₂₇NO₂

(2R,4aS,12aS)-2-methyl-2,3,6,7,9,10,12,12a-decahydro-4H,5H-benzo[e]pyrrole[3,2,1-ij]quinoline-4,11(1H)-dione

1,4-dioxaspiro[4.4]non-6-ene

2-((6R,7S)-7-(2-oxopropyl)-1,4-dioxaspiro[4.4]nonan-6-yl)acetaldehyde

Refernces

• 1、 Zeng, Chen,Zhao, Jingyun,Zhao, Gang. "Enantioselective divergent total syntheses of fawcettimine-type Lycopodium alkaloids". . p. 64 - 69. Retrieved 2014.
• 2、 Pan, Guojun,Williams, Robert M.. "Unified total syntheses of fawcettimine class alkaloids: Fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B". . p. 4801 - 4811. Retrieved 2012.
• 3、 Zeng, Chen,Zheng, Changwu,Zhao, Jingyun,Zhao, Gang. "Divergent total syntheses of (-)-lycopladine D, (+)-fawcettidine, and (+)-lycoposerramine Q". . p. 5846 - 5849. Retrieved 2013.