Aporphine

Base Information

• Chemical Name: Aporphine
• CAS No.: 478-57-9
• Molecular Formula: C₁₇H₁₇N
• Molecular Weight: 235.329
• UNII: 13NS2KTD6H
• DSSTox Substance ID: DTXSID80895017
• Nikkaji Number: J39.854C
• Wikipedia: Aporphine
• Wikidata: Q4780565
• Metabolomics Workbench ID: 55173
• Mol file: 478-57-9.mol

Synonyms:aporphine;aporphine hydrobromde, (+-)-isomer;aporphine, (+-)-isomer

Chemical Property of Aporphine

Chemical Property:

• Vapor Pressure: 1.04E-05mmHg at 25°C
• Boiling Point: 371.3°Cat760mmHg
• PKA: 8.28±0.20(Predicted)
• Flash Point: 160.5°C
• PSA: 3.24000
• Density: 1.127g/cm³
• LogP: 3.37660
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 235.136099547
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=C3C1CC4=CC=CC=C4C3=CC=C2

Technology Process of Aporphine

There total 23 articles about Aporphine 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: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolone (519-01-7) → (+/-)-Aporphine (478-57-9,710274-56-9,774507-78-7)

Guidance literature:

formaldehyd; 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolone; In methanol; water; at 20 ℃; for 0.5h;

With sodium tetrahydroborate; at 20 ℃; for 1h; Further stages.;

DOI:10.1016/j.tetlet.2004.04.194

Reference yield: 71.0%

5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxaldehyde (1418222-47-5) → (+/-)-Aporphine (478-57-9,710274-56-9,774507-78-7)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 6h; Reflux;

DOI:10.1016/j.bmc.2012.11.038

Reference yield:

methyl iodide (74-88-4) → (+/-)-Aporphine (478-57-9,710274-56-9,774507-78-7)

Guidance literature:

With potassium carbonate; In [⁽²⁾H₆]acetone;

upstream raw materials:

1-(2-aminobenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

formaldehyd

5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolone

6-tosyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolone

Refernces

• 1、 Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano. "A convenient formation of aporphine core via benzyne chemistry: Conformational analysis and synthesis of (R)-aporphine". supporting information. p. 6848 - 6851. Retrieved 2015/11/27.
• 2、 Nakamura, Seikou,Nakashima, Souichi,Tanabe, Genzo,Oda, Yoshimi,Yokota, Nami,Fujimoto, Katsuyoshi,Matsumoto, Takahiro,Sakuma, Rika,Ohta, Tomoe,Ogawa, Keiko,Nishida, Shino,Miki, Hisako,Matsuda, Hisashi,Muraoka, Osamu,Yoshikawa, Masayuki. "Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells". . p. 779 - 787. Retrieved 2013/02/25.