Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Base Information

• Chemical Name: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• CAS No.: 350014-18-5
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• DSSTox Substance ID: DTXSID10374946
• Mol file: 350014-18-5.mol

Synonyms:Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate;350014-18-5;SCHEMBL7124159;DTXSID10374946;HWLKUJXDHHWAIQ-UHFFFAOYSA-N;1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester;FT-0759041;EN300-316232;F14212;Methyl6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Chemical Property of Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Chemical Property:

• Boiling Point: 370℃
• PKA: 9.70±0.40(Predicted)
• Flash Point: 177℃
• PSA: 58.56000
• Density: 1.231
• LogP: 1.08080
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

99%,98% ^*data from raw suppliers

Methyl6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2=C(CCN1)C=C(C=C2)O

Technology Process of Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

There total 10 articles about Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 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: 100.0%

methanol (67-56-1) + rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (91523-50-1) → 1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester (350014-18-5)

Guidance literature:

With thionyl chloride; at 65 ℃;

DOI:10.1039/c7ra13148h

Reference yield: 75.0%

rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (91523-50-1) + acetyl chloride (75-36-5) → 1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester (350014-18-5)

Guidance literature:

In methanol;

Reference yield: 35.0%

methanol (67-56-1) + 2-(3-hydroxyphenyl)ethylamine hydrobromide (38449-59-1) + Glyoxilic acid (298-12-4) → 1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester (350014-18-5)

Guidance literature:

2-(3-hydroxyphenyl)ethylamine hydrobromide; Glyoxilic acid; With hydrogenchloride; In water; at 80 ℃; for 8h;

methanol; With chloro-trimethyl-silane; at 49 ℃; for 12h;

With sodium hydrogencarbonate; In water;

upstream raw materials:

methanol

rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

m-tyramine

3-Benzyloxybenzaldehyde

Downstream raw materials:

2-benzenesulfonyl-6-benzyloxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester

6-benzyloxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester

6-benzyloxy-2-(4-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester

6-benzyloxy-2-(2,5-dichloro-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester

Refernces

• 1、 Li, James J.,Wang, Haixia,Qu, Fucheng,Musial, Christa,Tino, Joseph A.,Robl, Jeffrey A.,Slusarchyk, Dorothy,Golla, Rajasree,Seethala, Ramakrishna,Dickinson, Kenneth,Giupponi, Leah,Grover, Gary,Sleph, Paul,Flynn, Neil,Murphy, Brian J.,Gordon, David,Kung, Melissa,Stoffel, Robert. "Tetrahydroisoquinoline 1-carboxamides as growth hormone secretagogues". . p. 1799 - 1802. Retrieved 2007/10/03.
• 2、 -. "Tetrahydroisoquinoline analogs as modulators of chemokine receptor activity". Page/Page column 38. . Retrieved 2010/11/29.