Nuciferine

Base Information

• Chemical Name: Nuciferine
• CAS No.: 475-83-2
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 295.381
• Hs Code.: 29389090
• European Community (EC) Number: 842-235-9
• UNII: W26UEB90B7
• DSSTox Substance ID: DTXSID40963862
• Nikkaji Number: J12.070G
• Wikipedia: Nuciferine
• Wikidata: Q7067904
• Metabolomics Workbench ID: 136581
• ChEMBL ID: CHEMBL464529
• Mol file: 475-83-2.mol

Synonyms:l-5,6-dimethoxyaporphine;nuciferine;nuciferine, (+-)-isomer;nuciferine, (S)-isomer

Chemical Property of Nuciferine

Chemical Property:

• Vapor Pressure: 1.27E-07mmHg at 25°C
• Melting Point: 165.5°C
• Refractive Index: 1.596
• Boiling Point: 430.7 °C at 760 mmHg
• PKA: 7.87±0.20(Predicted)
• Flash Point: 151.9 °C
• PSA: 21.70000
• Density: 1.15 g/cm³
• LogP: 3.39380
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 295.157228913
• Heavy Atom Count: 22
• Complexity: 401

Purity/Quality:

99%HPLC ^*data from raw suppliers

Nuciferine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC=CC=C43)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@H]1CC4=CC=CC=C43)OC)OC
• Uses: The lotus leaf alkaloid has the effect of weight loss and lipid reduction, and can be used for content determination/identification/pharmacological experiments.
• Description: Nuciferine is an aporphine alkaloid from Nelumbo lutea, the ba~e yields colourless crystals when crystallized from EtOH. It is laevorotatory, the following specific rotations having been recorded; [α] 22D- 157.5° and - 215°. The ultraviolet spectrum has three absorption maxima at 230, 272 and 310 mp. Two methoxyl groups and one methylimino group are present and the alkaloid may be characterized as the hydrochloride, m.p. 241°C (in vacuo) and the methiodide, m.p. 177-8°C. The optically inactive base has been synthesized and has m.p. 136-7°C, giving a hydrochloride in the form of small colourless prisms from H20, m.p. 258°C (dec.).

Technology Process of Nuciferine

There total 10 articles about Nuciferine 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: 88.0%

(R)-1,2-dimethoxy-4,5,6a,7-tetrahydrodibenzo[de,g]quinoline-6-carboxylic acid methyl ester → R-(-)-nuciferine (475-83-2,5868-18-8,16654-38-9,37659-75-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

DOI:10.1002/ejoc.200600674

Reference yield: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (4846-19-9,20454-22-2,37659-74-8,54750-04-8) → R-(-)-nuciferine (475-83-2,5868-18-8,16654-38-9,37659-75-9)

Guidance literature:

formaldehyd; (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; In methanol; water; at 20 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; water; at 20 ℃;

DOI:10.1016/j.tet.2020.131461

Reference yield:

(-)-N-methylasimilobine (6545-25-1,20827-76-3,33770-27-3,3153-55-7) + diazomethyl-trimethyl-silane (18107-18-1) → R-(-)-nuciferine (475-83-2,5868-18-8,16654-38-9,37659-75-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; hexane; acetonitrile; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2012.11.038

upstream raw materials:

diazomethane

(-)-N-methylasimilobine

diazomethyl-trimethyl-silane

2-(3,4-dimethoxyphenyl)-ethylamine

Downstream raw materials:

atherosperminine

(6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1,2-diol

dehydronuciferine

(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Refernces

Aporphine synthesis by Pschorr cyclization of aminophenols. An improved synthesis of a thalicarpine precursor.

10.1021/jo00942a048

The research presents an improved general synthesis of aporphines via Pschorr cyclization of 1-(2’-aminobenzyl)-7-hydroxy-l,2,3,4-tetrahydroisoquinolines. The key chemicals involved in this research include o-nitrotoluenes (2a-e), 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide, KO-t-Bu, Pd/C, Zn-H2SO4, diazomethane, and copper powder. The synthesis involves several steps: condensation of o-nitrotoluenes with 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide in the presence of KO-t-Bu to form 1-(2’-nitrobenzyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinolines (3a-e); reduction of these compounds with Pd/C or Zn-H2SO4 to obtain aminophenols (4a-f); and cyclization of the aminophenols to form 1-hydroxyaporphines (5a-f) using diazotization and copper powder. The final products include thalicmidine (5g), nuciferine (6a), glaucine (6g), and the thalicarpine precursor 6e. The synthesis is notable for achieving the highest yields reported to date for these compounds.

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