104967-54-6

Basic information

• Product Name: Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-
• CAS NO: 104967-54-6
• Molecular Formula: C19H23NO2
• Molecular Weight: 297.397
• Mol File: 104967-54-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-(104967-54-6)
• EPA Substance Registry System: Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-(104967-54-6)

Safety Data

• Hazardous Substances Data: 104967-54-6(Hazardous Substances Data)

Upstream product

• 77669-22-8 2-(3,4-dimethoxyphenylethenyl)quinoline 
• 552-89-6 2-nitro-benzaldehyde 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 1087319-45-6 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-(1-phenylethyl)-1,2,3,4-tetrahydroquinoline 
• 69731-27-7 (E)-1-bromo-2-(3,4-dimethoxyphenyl)ethene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 75903-25-2 2-(3',4'-dimethoxystyryl)quinoline 
• 91-63-4 2-methylquinoline 
• 95279-34-8 2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline 

Downstream Products

• 608525-25-3 (R)-2-(3’,4’-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline 
• 608525-32-2 (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline 
• 442-33-1 (R)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline 
• 442-33-1 (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline 
• 104967-55-7 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinolineanol 

Relevant articles and documents

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.