375395-24-7

Basic information

• Product Name: 2-(2-Benzo[1,3]dioxol-5-yl-ethyl)-1,2,3,4-tetrahydro-quinoline
• Synonyms: 2-(2-Benzo[1,3]dioxol-5-yl-ethyl)-1,2,3,4-tetrahydro-quinoline
• CAS NO: 375395-24-7
• Molecular Formula: C18H19NO2
• Molecular Weight: 281.34896
• Mol File: 375395-24-7.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-Benzo[1,3]dioxol-5-yl-ethyl)-1,2,3,4-tetrahydro-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Benzo[1,3]dioxol-5-yl-ethyl)-1,2,3,4-tetrahydro-quinoline(375395-24-7)
• EPA Substance Registry System: 2-(2-Benzo[1,3]dioxol-5-yl-ethyl)-1,2,3,4-tetrahydro-quinoline(375395-24-7)

Safety Data

• Hazardous Substances Data: 375395-24-7(Hazardous Substances Data)

Upstream product

• 1087319-47-8 2-[2-(1,3-benzodioxol-5-yl)ethyl]-1-(1-phenylethyl)-1,2,3,4-tetrahydroquinoline 
• 124902-95-0 2-(3',4'-methylenedioxyphenylethyl)quinoline 
• 27951-92-4 2-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)quinoline 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 91-63-4 2-methylquinoline 
• 77669-23-9 (E)-2-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)quinoline 
• 495-76-1 piperonol 
• 120-57-0 piperonal 
• 5344-90-1 2-Aminobenzyl alcohol 
• 55418-52-5 cassione 
• 75593-13-4 4-(3',4'-Methylenedioxyphenyl)-butan-2-ol 

Downstream Products

• 608525-33-3 (R)-2-( 3’,4’methylenedioxyphenethyl)-1,2,3,4-tetrahydroquinoline 
• 608525-33-3 (S)-2-[2-(3,4-methylenedioxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

NaCl as Catalyst and Water as Solvent: Highly E-Selective Olefination of Methyl Substituted N-Heteroarenes with Benzyl Amines and Alcohols

Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that in situ formed ClO2- is the active form of the catalyst. We have successfully carried out a 1 g scale reaction using this methodology, and five pharmaceutically relevant conjugated olefins were also synthesized by this method in moderate to good yields.

Iron-Catalyzed Coupling of Methyl N-Heteroarenes with Primary Alcohols: Direct Access to E-Selective Olefins

An efficient Fe-catalyzed system is reported for direct α-olefination of methyl-substituted N-heteroarenes with primary alcohols. The catalytic dehydrogenative coupling enables a series of functionalized E-olefinated N-heteroaromatics with excellent selectivity (>99%). Initial mechanistic studies including deuterium-labeling experiments provide evidence for the participation of the benzylic C-H/D bond of alcohols.

Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy

The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.