124525-61-7

Basic information

• Product Name: 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde
• Synonyms: 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde
• CAS NO: 124525-61-7
• Molecular Weight: 237.301
• Mol File: 124525-61-7.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde(124525-61-7)
• EPA Substance Registry System: 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde(124525-61-7)

Safety Data

• Hazardous Substances Data: 124525-61-7(Hazardous Substances Data)

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 124525-79-7 ethyl 2-cyano-3-<2-(1,2,3,4-tetrahydro-2-isoquinolinyl)phenyl>-2-propenoate 
• 1092982-53-0 5-phenyl-5,6,12,13-tetrahydro-4bH-isoquinolino[2,1-a]quinazoline 
• 1092982-54-1 5-benzyl-5,6,12,13-tetrahydro-4bH-isoquinolino[2,1-a]quinazoline 
• 1399147-10-4 C₂₃H₂₅NO₄ 
• 136638-72-7 5,6-dihydrodibenzo<2,3;7,8>indolizine 
• 1152514-66-3 (2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)methanol 
• 1435940-05-8 4b,13-dihydro-6H,12H-benzo[4,5][1,3]oxazino[2,3-a]isoquinolin-6-one 

Relevant articles and documents

Diastereoselective Spirocyclization via Intramolecular C(sp3)?H Bond Functionalization Triggered by Sequential [1,5]-Hydride Shift/Cyclization Process: Approach to Spiro-tetrahydroquinolines

A direct synthesis of spiro[5.5]and [5.4]-tetrahydroquinolines has been developed through C(sp3)?H bond functionalization triggered by sequential [1,5]- hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2-coumaranone, 4-hydroxycoumarin, 3-coumaranone, and 3-isochromanone. This protocol provides a Lewis acid catalyst-free straight forward one-pot reaction in cases of 2-coumaranone and 4-hydroxycoumarin, Lewis acid-catalyzed stepwise reaction for 3-coumaranone and 3-isochromanone to access a wide range of spiro-heterocycles in excellent to good yields and diastereoselectivity. (Figure presented.).

Catalyst-free photodecarbonylation ofortho-amino benzaldehyde

It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.

Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans

An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.