Dehydronuciferine

Base Information

• Chemical Name: Dehydronuciferine
• CAS No.: 7630-74-2
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.365
• DSSTox Substance ID: DTXSID801183819
• Nikkaji Number: J3.469.392G
• Wikidata: Q105124323
• Metabolomics Workbench ID: 46180
• ChEMBL ID: CHEMBL2316501
• Mol file: 7630-74-2.mol

Synonyms:Dehydronuciferine;7630-74-2;1,2-Dimethoxy-6-methyl-5,6-dihydro-4H-dibenzo[de,g]quinoline;5,6-Dihydro-1,2-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline;15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,13,15-heptaene;Dehydronuciferin;CHEMBL2316501;CHEBI:174097;DTXSID801183819;HY-N4261;NSC785154;ZB1875;AKOS037515219;NSC-785154;AC-34648;MS-24198;CS-0032561;F82186;15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,8,13(17),14-heptaene

Chemical Property of Dehydronuciferine

Chemical Property:

• Boiling Point: 493.0±45.0 °C(Predicted)
• PKA: 4.04±0.20(Predicted)
• PSA: 21.70000
• Density: 1.193±0.06 g/cm3(Predicted)
• LogP: 4.06750
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 293.141578849
• Heavy Atom Count: 22
• Complexity: 401

Purity/Quality:

≥98% ^*data from raw suppliers

Dehydronuciferine ≥99.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1=CC4=CC=CC=C43)OC)OC

Technology Process of Dehydronuciferine

There total 10 articles about Dehydronuciferine 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: 90.0%

nuciferine (5868-18-8) → dehydronuciferine (7630-74-2)

Guidance literature:

With iodine; sodium acetate; In 1,4-dioxane; for 2h; Reflux;

DOI:10.1021/acs.joc.5b01634

Reference yield: 50.0%

R-(-)-nuciferine (475-83-2,5868-18-8,16654-38-9,37659-75-9) → dehydronuciferine (7630-74-2)

Guidance literature:

With iodine; sodium acetate; In tetrahydrofuran; for 0.5h; Reflux;

DOI:10.1007/s00044-013-0905-9

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → dehydronuciferine (7630-74-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 2 h / 90 °C

2.1: trichlorophosphate / toluene / 2 h / 40 °C / Reflux

2.2: 0.17 h / 20 °C

3.1: pyridine / dichloromethane / 3 h / -50 °C / Inert atmosphere

4.1: cesium fluoride / acetonitrile / 24 h / 80 °C / Sealed tube

5.1: sodium tetrahydroborate / ethanol / 0.17 h / 20 °C / Inert atmosphere

6.1: methanol / 0.5 h / 20 °C

6.2: 1 h / 20 °C

7.1: iodine; sodium acetate / 1,4-dioxane / 2 h / Reflux

With pyridine; sodium tetrahydroborate; iodine; sodium acetate; cesium fluoride; trichlorophosphate; In 1,4-dioxane; methanol; ethanol; dichloromethane; toluene; acetonitrile; 2.1: |Bischler-Napieralski Reaction / 2.2: |Bischler-Napieralski Reaction;

DOI:10.1021/acs.joc.5b01634

upstream raw materials:

nuciferine

cepharadione B

R-(-)-nuciferine

2-(3,4-dimethoxyphenyl)-ethylamine