Graveolinine

Base Information

• Chemical Name: Graveolinine
• CAS No.: 4179-37-7
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.295
• UNII: 8J9MPP91DN
• DSSTox Substance ID: DTXSID201261279
• Nikkaji Number: J13.408B
• Wikidata: Q104396992
• Metabolomics Workbench ID: 44275
• ChEMBL ID: CHEMBL2205100
• Mol file: 4179-37-7.mol

Synonyms:Graveolinine;4179-37-7;2-(1,3-benzodioxol-5-yl)-4-methoxyquinoline;8J9MPP91DN;2-(1,3-benzodioxol-5-yl)-4-methoxy-quinoline;UNII-8J9MPP91DN;Quinoline, 2-(1,3-benzodioxol-5-yl)-4-methoxy-;Oprea1_242467;CHEMBL2205100;CHEBI:173977;DTXSID201261279;BDBM50540148;2-(2H-1,3-benzodioxol-5-yl)-4-methoxyquinoline;2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline, 9CI

Chemical Property of Graveolinine

Chemical Property:

• PSA: 40.58000
• LogP: 3.63910
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 279.08954328
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=NC2=CC=CC=C21)C3=CC4=C(C=C3)OCO4

Technology Process of Graveolinine

There total 21 articles about Graveolinine 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: 92.0%

2-(3,4-methylenedioxyphenyl)-1,4-dihydro-4-oxoquinoline (74054-38-9) + methyl iodide (74-88-4) → graveolinine (4179-37-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

DOI:10.1021/acs.orglett.0c00172

Reference yield: 86.0%

2-(benzo[d][1,3]dioxol-5-yl)-4-chloroquinoline + sodium methylate (124-41-4) → graveolinine (4179-37-7)

Guidance literature:

In methanol; at 140 ℃;

DOI:10.1021/acscatal.1c02055

Reference yield: 79.0%

methanol (67-56-1) + 3,4-methylenedioxyphenylethyne (57134-53-9) + 2-azidobenzaldehyde (16714-25-3) → graveolinine (4179-37-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; chemoselective reaction;

DOI:10.1021/acs.joc.6b02896

upstream raw materials:

Trimethyl orthoacetate

(E)-1-(benzo[d][1,3]dioxol-5-yl)-N-phenylmethanimine

(+/-)-2-(1,3-benzodioxol-5-yl)-2,3,dihydro-4(1H)-quinolinone

trimethyl orthoformate

Downstream raw materials:

graveoline

Refernces

• 1、 Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin. "NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines". . p. 7772 - 7779. Retrieved 2021/06/30.
• 2、 Luo, Wen,Lv, Jian-Wu,Wang, Ting,Zhang, Zhi-Yang,Guo, Hui-Yan,Song, Zhi-Yi,Wang, Chao-Jie,Ma, Jing,Chen, Yi-ping. "Synthesis, in vitro and in vivo biological evaluation of novel graveolinine derivatives as potential anti-Alzheimer agents". supporting information. . Retrieved 2019/11/29.