79261-58-8

Basic information

• Product Name: (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
• Synonyms: (S)-(+)-N-CBZ-1,2,3,4-TERTRAHYDRO ISOQUINOLINE-3-CARBOXYLIC ACID;N-ALPHA-CARBOBENZOXY-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;Z-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;Z-TIC-OH;Z-[3S]-1,2,3,4-TETRAHYDROISOQUINOLENE-3-CARBOXYLIC ACID;Z-D-[3S]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;(S)-(+)-2-(BENZYLOXYCARBONYL)-TETRAHY-DR O-3-ISOQUINOLINECARBOXYLIC ACID, 97%;(S)-N-Benzyloxycarbonyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
• CAS NO: 79261-58-8
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33
• Product Categories: Building Blocks for HIV Protease InhibitorsChiral Building Blocks;Cell Signaling Enzymes;Heterocyclic Building Blocks;HIV Protease Reagents&Envelope Proteins;Isoquinolines
• Mol File: 79261-58-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 137-141 °C
• Boiling Point: 451.38°C (rough estimate)
• Flash Point: 269.8oC
• Appearance: White to pale yellow/Solid
• Density: 1.2626 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 23.5 ° (C=2, MeOH)
• Storage Temp.: Store at 0-5°C
• PKA: 3.86±0.20(Predicted)
• CAS DataBase Reference: (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID(79261-58-8)
• EPA Substance Registry System: (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID(79261-58-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-36/37/39
• Hazardous Substances Data: 79261-58-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

(3S)-2-Carbobenzoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid is a reagent in the preparation of antibacterial studies of peptide deformylase inhibitor BB-3497 and its P2’ and P3’ analogs.

InChI:InChI=1/C18H17NO4/c20-17(21)16-10-14-8-4-5-9-15(14)11-19(16)18(22)23-12-13-6-2-1-3-7-13/h1-9,16H,10-12H2,(H,20,21)/t16-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 77497-95-1 (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 63-91-2 L-phenylalanine 
• 74163-81-8 L-Tic-OH 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 1238365-80-4 (S)-benzyl 3-((S)-1-phenylethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1238365-78-0 (S)-benzyl 3-(isopropylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 254102-04-0 (S)-benzyl 3-(methylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1238365-76-8 (S)-benzyl 3-(benzhydrylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1238365-75-7 (S)-benzyl 3-(benzylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1238365-77-9 (S)-benzyl 3-(phenylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1383448-94-9 (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide) 
• 1383448-95-0 (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-o-tolyl-1,2,3,4-tetra-hydroisoquinoline-3-carboxamide) 
• 1383448-96-1 (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide) 
• 1383448-97-2 (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-(2,6-diisopropylphe-nyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide) 
• 1383448-89-2 (S)-benzyl 3-(o-tolylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1383448-90-5 (S)-benzyl 3-(2,6-dimethylphenylcarbamoyl)-3,4-dihydro-isoquinoline-2(1H)-carboxylate 
• 1383448-92-7 (S)-N-O-tolyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1383448-93-8 (S)-N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 

Relevant articles and documents

New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)

Two new strategies for the efficient synthesis of racemic 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (TicP) (±)-2 have been developed. The first strategy involves the electron-transfer reduction of the easily obtained α,β-dehydro phosphonophenylalanine followed by a Pictet–Spengler cyclization. The second strategy involves a radical decarboxylation–phosphorylation reaction on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic). In both strategies, the highly electrophilic N-acyliminium ion is formed as a key intermediate, and the target compound is obtained in good yield using mild reaction conditions and readily available starting materials, complementing existing methodologies and contributing to the easy accessibility of (±)-2 for further research.

Discovery and Characterization of Biased Allosteric Agonists of the Chemokine Receptor CXCR3

In this work we report a design, synthesis, and detailed functional characterization of unique strongly biased allosteric agonists of CXCR3 that contain tetrahydroisoquinoline carboxamide cores. Compound 11 (FAUC1036) is the first strongly biased allosteric agonist of CXCR3 that selectively induces weak chemotaxis and leads to receptor internalization and the β-arrestin 2 recruitment with potency comparable to that of the chemokine CXCL11 without any activation of G proteins. A subtle structural change (addition of a methoxy group, 14 (FAUC1104)) led to a contrasting biased allosteric partial agonist that activated solely G proteins, induced chemotaxis, but failed to induce receptor internalization or β-arrestin 2 recruitment. Concomitant structure-activity relationship studies indicated very steep structure-activity relationships, which steer the ligand bias between the β-arrestin 2 and G protein pathway. Overall, the information presented provides a powerful platform for further development and rational design of strongly biased allosteric agonists of CXCR3.

Microwave-assisted synthesis of guanidine organocatalysts bearing a tetrahydroisoquinoline framework and their evaluation in Michael addition reactions

The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and β-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee). Copyright