4179-37-7

Basic information

• Product Name: 2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline
• Synonyms: 2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline;Graveolinine
• CAS NO: 4179-37-7
• Molecular Formula: C17H13 N O3
• Molecular Weight: 0
• Mol File: 4179-37-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline(4179-37-7)
• EPA Substance Registry System: 2-(1,3-Benzodioxol-5-yl)-4-methoxyquinoline(4179-37-7)

Safety Data

• Hazardous Substances Data: 4179-37-7(Hazardous Substances Data)

Usage

Chemical Class

Quinolines

Derivative

Bisbenzylisoquinoline alkaloid

Structure

A derivative of quinoline with a methoxy group at the 4-position and a benzodioxol ring at the 2-position.

Pharmacological Properties

Anti-inflammatory, anti-cancer, and anti-microbial activities

Potential Use

Treatment for various diseases and conditions

Interest in Pharmaceutical Industry

Unique structure and potential biological activities make it a subject of interest for further research and development.

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 853099-64-6 (E)-1-(benzo[d][1,3]dioxol-5-yl)-N-phenylmethanimine 
• 135762-53-7 (+/-)-2-(1,3-benzodioxol-5-yl)-2,3,dihydro-4(1H)-quinolinone 
• 149-73-5 trimethyl orthoformate 
• 14547-98-9 4-methoxyquinoline-N-oxide 
• 607-31-8 4-methoxyquinoline 
• 67-56-1 methanol 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 16714-25-3 2-azidobenzaldehyde 
• 615-43-0 2-iodophenylamine 
• 74054-38-9 2-(3,4-methylenedioxyphenyl)-1,4-dihydro-4-oxoquinoline 
• 74-88-4 methyl iodide 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 94-53-1 Piperonylic acid 

Downstream Products

• 485-61-0 graveoline 

Relevant articles and documents

QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF

The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

Novel synthesis of graveoline and graveolinine

Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT (Figure presented.).