Dihydroevocarpine

Base Information

• Chemical Name: Dihydroevocarpine
• CAS No.: 15266-35-0
• Molecular Formula: C23H35NO
• Molecular Weight: 341.5301
• DSSTox Substance ID: DTXSID301316469
• Nikkaji Number: J438.811I
• Wikidata: Q104394044
• Metabolomics Workbench ID: 123856
• ChEMBL ID: CHEMBL1643843
• Mol file: 15266-35-0.mol

Synonyms:Dihydroevocarpine;15266-35-0;1-methyl-2-tridecylquinolin-4-one;CHEMBL1643843;DTXSID301316469;HY-N2517;1-methyl-2-tridecyl-quinolin-4-one;AKOS032949028;AC-34692;MS-25225;CS-0022788;FT-0761788;E88607;3.2.8.1.1-Methyl-2-tridecyl-4(1H)-quinolone

Chemical Property of Dihydroevocarpine

Chemical Property:

• Melting Point: 68-69℃
• Boiling Point: 447.0±45.0 °C(Predicted)
• PKA: 2.52±0.70(Predicted)
• PSA: 22.00000
• Density: 0.964±0.06 g/cm3(Predicted)
• LogP: 6.39200
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 341.271864740
• Heavy Atom Count: 25
• Complexity: 414

Purity/Quality:

98%Min ^*data from raw suppliers

Dihydroevocarpine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC1=CC(=O)C2=CC=CC=C2N1C

Technology Process of Dihydroevocarpine

There total 15 articles about Dihydroevocarpine 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: 100.0%

evocarpine (15266-38-3,98393-27-2) → dihydroevocarpine (15266-35-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h; under 1292.9 Torr;

Reference yield: 95.0%

1-methyl-2-[(Z)-4'-tridecenyl]-4(1H)-quinolone (250293-82-4) → dihydroevocarpine (15266-35-0)

Guidance literature:

With 10% palladium on activated carbon; hydrogen; In ethanol; for 24h;

DOI:10.1016/j.bmc.2010.10.060

Reference yield: 74.0%

1-methyl-4-quinolone (83-54-5) + 1-tridecene (2437-56-1) → dihydroevocarpine (15266-35-0)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In toluene; at 80 ℃; for 11h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201200922

upstream raw materials:

pentadecan-2-one

N-Methylisatoic anhydride

evocarpine

8-bromooctanoic acid

Refernces

• 1、 Tamura, Ryuichi,Yamada, Yuuya,Nakao, Yoshiaki,Hiyama, Tamejiro. "Alkylation of pyridone derivatives by nickel/Lewis acid catalysis". supporting information; experimental part. p. 5679 - 5682. Retrieved 2012/07/14.
• 2、 Coppola, Gary M.. "The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 17. Synthesis of 2-Alkyl-4-quinolone Alkaloids via a One-step Reaction of N-Methylisatoic Anhydride with Methyl Ketone Enolates". . p. 491 - 494. Retrieved 2007/10/02.