N-Nornuciferine

Base Information

• Chemical Name: N-Nornuciferine
• CAS No.: 4846-19-9
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.354
• European Community (EC) Number: 836-647-8
• ChEMBL ID: CHEMBL1164391
• Metabolomics Workbench ID: 122435
• Nikkaji Number: J14.264F
• Wikidata: Q104375588
• Mol file: 4846-19-9.mol

Synonyms:N-Nornuciferine;4846-19-9;(R)-Nornuciferine;Daechualkaloid E;(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;1,2-Dimethoxynoraporphine;Sanjoinine Ia;N-Desmethylnuciferine;6a.beta.-Noraporphine, 1,2-dimethoxy-;CHEMBL1164391;QQKAHDMMPBQDAC-CQSZACIVSA-N;HY-N2129;MFCD26406146;1,2-Dimethoxy-6a.beta.-noraporphine;4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-, (R)-;AC-34564;AS-82975;CS-0018680;A871917;(R)-5,6,6a,7-Tetrahydro-1,2-dimethoxy-4H-dibenzo[de,g]quinoline;1,2-Dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline #;4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-, (6aR)-;(9R)-15,16-dimethoxy-10-azatetracyclo[7.7.1.0?,?.0??,??]heptadeca-1(16),2,4,6,13(17),14-hexaene

Chemical Property of N-Nornuciferine

Chemical Property:

• Melting Point: 128-129℃
• Boiling Point: 446.4±45.0 °C(Predicted)
• PKA: 8.29±0.20(Predicted)
• PSA: 30.49000
• Density: 1.163±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.44250
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 281.141578849
• Heavy Atom Count: 21
• Complexity: 374

Purity/Quality:

≥98% ^*data from raw suppliers

N-Nornuciferine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C3C(CC4=CC=CC=C42)NCCC3=C1)OC
• Isomeric SMILES: COC1=C(C2=C3[C@@H](CC4=CC=CC=C42)NCCC3=C1)OC
• Uses: N-?Nornuciferine is an alkaloid extracted from the Hottuynia cordata displaying anti-inflammatory activity.

Technology Process of N-Nornuciferine

There total 9 articles about N-Nornuciferine 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: 68.0%

(R)-1,2-dimethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl ((S)-1-tosylpyrrolidin-2-yl)methanone → (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)

Guidance literature:

With lithium hydroxide; In ethanol; water; at 180 ℃; for 1h; Sealed tube; Microwave irradiation;

DOI:10.1016/j.tet.2020.131461

Reference yield: 53.0%

tert-butyl (R)-4,5,6a,7-tetrahydro-1,2-dimethoxydibenzo[de,g]quinoline-6-carboxylate → (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)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200600674

Reference yield: 40.0%

(6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (104385-30-0) → (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)

Guidance literature:

With ferrous(II) sulfate heptahydrate; In methanol; at 0 - 20 ℃; for 12h;

DOI:10.1007/s00044-013-0905-9

upstream raw materials:

R-(-)-nuciferine

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

2-(3,4-dimethoxyphenyl)-ethylamine

N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide

Downstream raw materials:

caaverine

R-(-)-nuciferine

Refernces

• 1、 Yang, Zhongduo,Song, Zhuwen,Xue, Weiwei,Sheng, Jie,Shu, Zongmei,Shi, Yin,Liang, Jibei,Yao, Xiaojun. "Synthesis and structure-Activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors". . p. 3178 - 3186. Retrieved 2014/05/06.