Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Base Information

• Chemical Name: Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate
• CAS No.: 59604-96-5
• Molecular Formula: C12H14 O3
• Molecular Weight: 206.23800
• Hs Code.: 2918199090
• European Community (EC) Number: 676-638-4
• DSSTox Substance ID: DTXSID50469244
• Nikkaji Number: J1.950.526J
• Wikidata: Q82296872
• Mol file: 59604-96-5.mol

Synonyms:Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate;59604-96-5;SCHEMBL6608334;YSCK0377;DTXSID50469244;FGZPUQMMDVJQQN-UHFFFAOYSA-N;Methyl2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate;MFCD09258894;2-Hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester;AKOS015957528;AS-71990;VU0549383-1;EN300-203432;F72410;methyl 2-hydroxy-5,6,7,8-tetrahydro-1-naphthoate;F9995-0491;Z1509587571;Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate, 97%;2-Hydroxy-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property of Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Chemical Property:

• Melting Point: 40-43℃
• PSA: 46.53000
• LogP: 2.05760
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

methyl2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC2=C1CCCC2)O

Technology Process of Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

There total 9 articles about Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-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: 72.0%

methyl 7-(fur-2-yl)hept-2-ynoate → 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (59604-96-5)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at 40 ℃; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.5b02412

Reference yield: 70.0%

methyl 2-hydroxy-1-naphthoate (947-65-9) → 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (59604-96-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; at 60 ℃; for 2.5h; under 77572.2 Torr;

DOI:10.1021/jm0601001

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (59604-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 22.2 g / sodium hydride, ethanol / diethyl ether / 2 h

2: 1.) triethylamine, 2.) titanium tetrachloride / 1.) hexane, 2.) dichloromethane, -78 deg C, 3 h

With ethanol; titanium tetrachloride; sodium hydride; triethylamine; In diethyl ether;

DOI:10.1021/ja00530a038

upstream raw materials:

2-methoxy-5,6,7,8-tetrahydro-[1]naphthoic acid methyl ester

chloro-trimethyl-silane

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

2-(hydroxymethylene)cyclohexanone

Downstream raw materials:

N-(1-cyano-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

N-[1-(1H-tetrazol-5-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]-benzenesulfonamide

2-benzenesulfonylamino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid amide

2-(benzhydrylidene-amino)-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester

Refernces

• 1、 -. "TETRAZOLE COMPOUNDS AND METHODS OF MAKING AND USING SAME". Page/Page column 52. . Retrieved 2012/08/08.
• 2、 Sheppard, George S.,Wang, Jieyi,Kawai, Megumi,Fidanze, Steve D.,BaMaung, Nwe Y.,Erickson, Scott A.,Barnes, David M.,Tedrow, Jason S.,Kolaczkowski, Lawrence,Vasudevan, Anil,Park, David C.,Wang, Gary T.,Sanders, William J.,Mantei, Robert A.,Palazzo, Fabio,Tucker-Garcia, Lora,Lou, Pingping,Zhang, Qian,Park, Chang H.,Kim, Ki H.,Petros, Andrew,Olejniczak, Edward,Nettesheim, David,Hajduk, Phillip,Henkin, Jack,Lesniewski, Richard,Davidsen, Steven K.,Bell, Randy L.. "Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: A structural basis for the reduction of albumin binding". . p. 3832 - 3849. Retrieved 2007/10/03.