(S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Base Information

• Chemical Name: (S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• CAS No.: 128502-56-7
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Hs Code.: 29334990
• European Community (EC) Number: 802-765-3
• Nikkaji Number: J469.050H
• Wikidata: Q76145998
• Mol file: 128502-56-7.mol

Synonyms:128502-56-7;(S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;(3S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;(S)-1,2,3,4-TETRAHYDRO-7-HYDROXYISOQUINOLINE-3-CARBOXYLIC ACID;L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;128506-12-7;7-Hydroxy-(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-7-hydroxy-, (3S)-;MFCD00144534;(S)-1,2,3,4-TETRAHYDRO-7-HYDROXYISOQUINOLINE-3-CARBOXYLIC ACID 98per cent;(3S)-7-hydroxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid;(3S)-1,2,3,4-Tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid dihydrate;H-7-Hydroxy-Tic-OH;H-L-Tic(7-OH)-OH;SCHEMBL539874;H-Tic(7-OH)-OH.nH2O;AKOS005258674;CS-W009083;AC-22000;DS-11335;EN300-2008672;W-205298;(3s)-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid;(S)-1,2,3,4-Tetrahydro-7-hydroxy-3-isoquinolinecarboxylic acid;(S)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid;L-7-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID;l-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, AldrichCPR

Chemical Property of (S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Chemical Property:

• Appearance/Colour: off-white to beige or grey crystalline powder
• Vapor Pressure: 4.06E-09mmHg at 25°C
• Melting Point: 273-275 °C
• Refractive Index: 1.612
• Boiling Point: 456.281 °C at 760 mmHg
• PKA: 2.19±0.20(Predicted)
• Flash Point: 229.751 °C
• PSA: 69.56000
• Density: 1.351 g/cm³
• LogP: 0.81990
• Storage Temp.: 2-8°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NCC2=C1C=CC(=C2)O)C(=O)O
• Isomeric SMILES: C1[C@H](NCC2=C1C=CC(=C2)O)C(=O)O
• Uses: L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid is a possible histone deacetylases (HDACs) inhibitor. It is used in the design of boronic acid-based autotaxin inhibitors.

Technology Process of (S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

There total 4 articles about (S)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

(S)-1,2,3,4-Tetrahydro-7-hydroxy-6,8-diiodoisoquinoline-3-carboxylic acid (142335-40-8) → (3S)-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid (128502-56-7)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; water; at 25 ℃; for 3h; under 2068.6 Torr;

DOI:10.1055/s-1992-26135

Reference yield:

3,5-diiodo-l-tyrosine (300-39-0) → (3S)-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid (128502-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / conc. HCl / 1,2-dimethoxy-ethane / 18.5 h / 72 °C

2: 73 percent / hydrogen, Et₃N / 10 percent Pd-C / ethanol; H₂O / 3 h / 25 °C / 2068.6 Torr

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol; water;

DOI:10.1055/s-1992-26135

Reference yield:

(S)-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride → (3S)-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid (128502-56-7)

Guidance literature:

(S)-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride; With palladium 10% on activated carbon; hydrogen; triethylamine; In ethanol; water; for 4h;

With hydrogenchloride; In ethanol; water; pH=6;

DOI:10.1016/j.bmc.2010.01.060

upstream raw materials:

(S)-1,2,3,4-Tetrahydro-7-hydroxy-6,8-diiodoisoquinoline-3-carboxylic acid

3,5-diiodo-l-tyrosine

Dimethoxymethane

L-tyrosine

Downstream raw materials:

(3S)-N-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid

(3S)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid

(S)-(4-(((2-(4-fluorobenzyl)-1,3-dioxo-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolin-7-yl)oxy)methyl)phenyl)boronic acid

(S)-2-(4-fluorobenzyl)-7-hydroxy-10,10a-dihydroimidazo-[1,5-b]isoquinoline-1,3(2H,5H)-dione

Refernces

• 1、 Verschueren,Toth,Tourwe,Lebl,Van Binst,Hruby. "A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue". . p. 458 - 460. Retrieved 1992.
• 2、 -. "NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF". Paragraph 0925-0927. . Retrieved 2019/12/24.