180272-31-5

Basic information

• Product Name: 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, ethyl ester
• CAS NO: 180272-31-5
• Molecular Formula: C18H19NO2
• Molecular Weight: 281.354
• Mol File: 180272-31-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, ethyl ester(180272-31-5)
• EPA Substance Registry System: 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, ethyl ester(180272-31-5)

Safety Data

• Hazardous Substances Data: 180272-31-5(Hazardous Substances Data)

Upstream product

• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 541-41-3 chloroformic acid ethyl ester 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 3230-65-7 3,4-dihydroisoquinoline 
• 960-16-7 tributylphenylstannane 

Downstream Products

• 180272-14-4 quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate 
• 180272-14-4 (1R)-quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate 
• 180272-14-4 (S,R)-((R)-quinuclidin-3-yl) 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant articles and documents

Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: A multicomponent synthesis of α-substituted amides

A copper-catalyzed cross-coupling of organotin reagents with imines and acid chlorides is reported. The reaction proceeds efficiently with a range of vinyl-, alkyl-, aryl- and heteroaryl-substituted organostannanes as well as a diverse set of imines of non-enolizable aldehydes. Use of chloroformates also allows for the formation of N-protected α-substituted amines. This chemistry has been applied to the synthesis of isoquinoline alkaloid derivatives through the activation of cyclic imines.

Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists

In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

Application of the intermolecular α-amido-alkylation reaction for the synthesis of tertiary amides and 1-substituted 2-acyltetrahydroisoquinolines. Synthesis of (±)-carnegine

Adducts 4 of Schiff bases and 3,4-dihydroisoquinolines with acyl chlorides react with Grignard reagents 5 in an intermolecular α-amidoalkylation reaction to the corresponding tertiary amides or 1-substituted 2-acyltetrahydroisoquinolines.