106181-28-6

Basic information

• Product Name: 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester
• Synonyms: Ethyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylate;REF DUPL: 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester;2-ethyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate;1-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, ethyl ester
• CAS NO: 106181-28-6
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 106181-28-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 313.4 °C at 760 mmHg
• Flash Point: 143.3 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 0.000499mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester(106181-28-6)
• EPA Substance Registry System: 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester(106181-28-6)

Safety Data

• Hazardous Substances Data: 106181-28-6(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester is a chemical compound with the molecular formula C12H17NO2. It is a derivative of isoquinoline and is commonly used as a precursor in the synthesis of various pharmaceutical compounds. 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester is known for its potential pharmacological properties and has been studied for its potential use in the development of new drugs. It is also used in organic chemistry research as a building block for the synthesis of other compounds. Additionally, it has been reported as a potential ligand for various biological targets and has shown potential as an anticancer agent in preliminary studies. Overall, 1,2,3,4-Tetrahydro-1-isoquinoline carboxylic acid ethyl ester is a versatile compound with a wide range of potential applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C12H15NO2/c1-2-15-12(14)11-10-6-4-3-5-9(10)7-8-13-11/h3-6,11,13H,2,7-8H2,1H3

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 541-41-3 chloroformic acid ethyl ester 
• 50458-78-1 ethyl isoquinoline-1-carboxylate 
• 66384-49-4 N-(2-(2-iodophenyl)ethyl)amine 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 41034-52-0 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 64-17-5 ethanol 

Downstream Products

• 103733-35-3 <3S-<2>,3R*>-2-<2-<<1-(ethoxycarbonyl)-3-phenylpropyl>amino>-1-oxopropyl>-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, ethyl ester 
• 195719-62-1 2-Benzoyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester 
• 206118-06-1 3,4-Dihydro-1H-isoquinoline-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester 
• 950580-38-8 (S)-ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate 
• 950580-38-8 C₁₂H₁₅NO₂ 
• 151004-92-1 (S)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 151004-93-2 (R)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 135526-78-2 (-)-Praziquantel 
• 55375-92-3 (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 55375-96-7 C₁₇H₁₈N₂O 
• 22914-95-0 2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 

Relevant articles and documents

Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

A dynamic kinetic resolution method for the preparation of enantiopure 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (R)-2 was developed involving the CAL-B-catalyzed enantioselective hydrolysis of the corresponding ethyl ester (±)-1 in toluene/acetonitrile (4:1) containing 1 equiv of added water and 0.25 equiv of dipropylamine. This method allowed the preparation of (R)-2 (ee = 96%) with 80% isolated yield. The kinetic resolution of (±)-1 in diisopropyl ether at 3 °C afforded both enantiomers with ee ≥92%.

Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline α-amino acid synthesis

The scope of aryl radical additions to the nitrogen of azomethines is described. Aryl, trifluoromethyl alkyl, and α,β-unsaturated ketimines engage in regioselective aryl-nitrogen bond formation via 5-exo cyclizations of an aryl radical to azomethine nitrogen. Selectivity for carbon-nitrogen over carbon-carbon bond formation is generally high (>95:5) and competes only with direct aryl radical reduction by stannane (0-10%). α-Ketoimines are a promising new class of carbon radical acceptors for which no competitive aryl radical reduction is observed. The reaction conditions are pH-neutral and are therefore among the mildest methods available for amination of an aromatic ring. The ketimines examined did not suffer from competitive reduction by stannane, offering an advantage over the use of diazo and azide functional groups as nitrogen sources for carbon radicals. The free radical-mediated aryl amination was sequenced with the O'Donnell phase transfer-catalyzed enantioselective alkylation strategy of glycinyl imine to provide either enantiomer of indoline α-amino acids with high ee. These new constrained phenyl alanine derivatives are now readily available for evaluation across a variety of applications.

Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types

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