methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

Base Information

• Chemical Name: methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate
• CAS No.: 274673-50-6
• Molecular Formula: C20H20O2
• Molecular Weight: 292.378
• DSSTox Substance ID: DTXSID001148823
• Mol file: 274673-50-6.mol

Synonyms:274673-50-6;methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate;DTXSID001148823;A849699;3-p-Tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester;methyl 3-(4-methylphenyl)-8,9-dihydro-7H-benzo[7]annulene-6-carboxylate;Methyl 6,7-dihydro-2-(4-methylphenyl)-5H-benzocycloheptene-8-carboxylate

Chemical Property of methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

Chemical Property:

• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 292.146329876
• Heavy Atom Count: 22
• Complexity: 417

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=CC3=C(CCCC(=C3)C(=O)OC)C=C2

Technology Process of methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

There total 16 articles about methyl 2-p-tolyl-6,7-dihydro-5H-benzo[7]annulene-8-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: 99.0%

4-methylphenylboronic acid (5720-05-8) + methyl 2-bromo-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (229007-63-0) → 3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester (274673-50-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,2-dimethoxyethane; at 100 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4ob02397h

Reference yield: 77.0%

5-methanesulfonyloxy-3-p-tolyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid methyl ester → 3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester (274673-50-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jm9906264

Reference yield:

carbonic acid dimethyl ester (616-38-6) + 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (229006-86-4) → 3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester (274673-50-6)

Guidance literature:

carbonic acid dimethyl ester; 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one; With sodium methylate; for 2h; Reflux; Large scale;

With sodium tetrahydroborate; In tetrahydrofuran; water-d2; at -15 - -5 ℃; for 2.5h; Further stages; Inert atmosphere; Large scale;

DOI:10.1021/op000074v

upstream raw materials:

ethyl glutaroyl chloride

bromobenzene

4-bromo-δ-oxobenzenepentanoic acid

3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

Downstream raw materials:

TAK-779

2-(4-methylphenyl)-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-6,7-dihydro-5H-benzo[a][7]annulene-8-carboxamide

N-(4-hydroxymethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide

N-(4-chloromethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide