151004-92-1

Basic information

• Product Name: (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID
• Synonyms: (S)-1,2,3,4-TETRAHYDRO-1-ISOQUINOLINE CARBOXYLIC ACID;(S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID;T11220;1-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, (1S)-;(1S)-1,2,3,4-Tetrahydro-1-isochinolinecarboxylic acid;(1S)-1,2,3,4-tetrahydro-1-IsoQuinolinecarboxylic acid
• CAS NO: 151004-92-1
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.2
• Product Categories: pharmacetical
• Mol File: 151004-92-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 370.7 °C at 760 mmHg
• Flash Point: 178 °C
• Appearance: /
• Density: 1.225 g/cm³
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• PKA: 1.84±0.20(Predicted)
• CAS DataBase Reference: (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(151004-92-1)
• EPA Substance Registry System: (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(151004-92-1)

Safety Data

• Hazardous Substances Data: 151004-92-1(Hazardous Substances Data)

Usage

General Description

(S)-1,2,3,4-Tetrahydro-isoquinoline-1-carboxylic acid is a chemical compound with potential pharmacological activities. It is a tetrahydroisoquinoline derivative and a precursor in the biosynthesis of alkaloids. It may exhibit neuroprotective and anti-inflammatory properties, making it a potential candidate for the treatment of neurological disorders and inflammatory conditions. (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID has also been studied for its potential role in the synthesis of novel psychoactive substances and pharmaceutical agents. Further research is needed to explore its full range of biological activities and potential applications in medicine and drug development.

InChI:InChI=1/C10H11NO2/c12-10(13)9-8-4-2-1-3-7(8)5-6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m0/s1

Upstream product

• 106181-28-6 ethyl (+/-)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 
• 92932-74-6 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid hydrochloride 

Downstream Products

• 1432065-37-6 benzyl-(1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylate 
• 908249-20-7 2-[(1S)-1,2,3,4-tetrahydroisoquinolin-1-ylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 1432065-36-5 C₁₈H₁₉NO₃ 
• 151004-94-3 Boc-L-1,2,3,4-tetrahydroisoquinoline carboxylic acid 

Relevant articles and documents

A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids are important chiral building blocks in the pharmaceutical and fine chemical industries. However, the existing chemo-enzymatic deracemization method employing d-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) suffers from the requirement for a large excess of a nonselective chemical reducing agent. To explore an alternative method, we envisaged a concurrent biocatalytic oxidation and reduction cascade in one pot. Herein, we report a novel biocatalytic route for the asymmetric reduction of 3,4-dihydroisoquinoline-1-carboxylic acids employing Δ1-piperidine-2-carboxylate/Δ1-pyrrolidine-2-carboxylate reductase from Pseudomonas putida KT2440 (PpDpkA) as a biocatalyst, yielding the corresponding (S)-1-carboxyl-substituted tetrahydroisoquinolines with high conversions and enantiomeric excess (>99% ee). By combining FsDAAO and PpDpkA in one pot, a fully biocatalytic method was demonstrated for the deracemization of a range of racemic 1-carboxyl substituted tetrahydroisoquinolines to produce the corresponding (S)-enantiomers with >99% conversions and >99% ee. Furthermore, preparative-scale biotransformation of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid gave the (S)-enantiomer with 89% isolated yield and >99% ee. Taken together, we provide an enantioselective biocatalytic redox cascade method for the one-pot synthesis of enantiopure 1,2,3,4-tetrahydroisoquinoline carboxylic acids.

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%.

Substituted iminoacid derivatives, process for preparing them and their use as enzyme inhibitors

Bicyclic imino acids, particularly 2-carboxylic acid derivatives of azabicycloalkanes and process for preparing them. These compounds have therapeutical activity and may be used as medicines, particularly as cardiovascular and antihypertensive drugs in human or veterinary medicine.