189094-06-2

Basic information

• Product Name: (R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID T-BUTYL ESTER
• Synonyms: 3-ISOQUINOLINECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-, 1,1-DIMETHYLETHYL ESTER;(R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID T-BUTYL ESTER;tert-Butyl (R)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylate
• CAS NO: 189094-06-2
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• Mol File: 189094-06-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 331.626 °C at 760 mmHg
• Flash Point: 154.362 °C
• Appearance: /
• Density: 1.063 g/cm³
• PKA: 7.65±0.40(Predicted)
• CAS DataBase Reference: (R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID T-BUTYL ESTER(189094-06-2)
• EPA Substance Registry System: (R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID T-BUTYL ESTER(189094-06-2)

Safety Data

• Hazardous Substances Data: 189094-06-2(Hazardous Substances Data)

Usage

General Description

The chemical (R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid T-butyl ester, also known as TBE-THIQ, is a derivative of isoquinoline that is often used in organic synthesis and pharmaceutical research. It is a chiral compound, meaning it has a non-super imposable mirror image, and the (R) configuration in its name indicates its chirality. TBE-THIQ has been studied for its potential use in the development of new drugs, particularly in the treatment of Parkinson's disease and other neurological disorders. It is also used as a precursor in the synthesis of various organic molecules and pharmaceuticals.

Upstream product

• 74163-81-8 L-Tic-OH 
• 115-11-7 isobutene 
• 77497-95-1 (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 79276-05-4 Z-Tic-OtBu 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 79276-06-5 THIQ tert-butyl ester PTSA salt 
• 82586-60-5 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester, hydrochloride 
• 103733-65-9 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 91-13-4 α,α'-dibromo-o-xylene 

Relevant articles and documents

Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives

A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.

Concise, catalytic asymmetric synthesis of tetrahydroisoquinoline- and dihydroisoquinoline-3-carboxylic acid derivatives

Catalytic asymmetric synthesis of tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives 1 has been accomplished by the successful utilization of phase-transfer catalysis of the C2-symmetric chiral quaternary ammonium bromides. Our approach also enables facile synthesis of quaternary isoquinoline derivatives 2 and 3 with high enantiomeric purities.

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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