5H-Benzocyclohepten-5-one, 6,7,8,9-tetrahydro-3-(4-methylphenyl)-

Base Information

• Chemical Name: 5H-Benzocyclohepten-5-one, 6,7,8,9-tetrahydro-3-(4-methylphenyl)-
• CAS No.: 229006-86-4
• Molecular Formula: C18H18O
• Molecular Weight: 250.34
• DSSTox Substance ID: DTXSID70436059
• Nikkaji Number: J1.460.177E
• Wikidata: Q82251252
• Mol file: 229006-86-4.mol

Synonyms:229006-86-4;5H-BENZOCYCLOHEPTEN-5-ONE, 6,7,8,9-TETRAHYDRO-3-(4-METHYLPHENYL)-;3-(4-METHYLPHENYL)-6,7,8,9-TETRAHYDROBENZO[7]ANNULEN-5-ONE;3-(4-Methylphenyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-5-one;SCHEMBL5209716;DTXSID70436059

Chemical Property of 5H-Benzocyclohepten-5-one, 6,7,8,9-tetrahydro-3-(4-methylphenyl)-

Chemical Property:

• PSA: 17.07000
• LogP: 4.57110
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 250.135765193
• Heavy Atom Count: 19
• Complexity: 314

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=CC3=C(CCCCC3=O)C=C2

Technology Process of 5H-Benzocyclohepten-5-one, 6,7,8,9-tetrahydro-3-(4-methylphenyl)-

There total 10 articles about 5H-Benzocyclohepten-5-one, 6,7,8,9-tetrahydro-3-(4-methylphenyl)- 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: 98.0%

3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (87779-78-0) + 4-methylphenylboronic acid (5720-05-8) → 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (229006-86-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; toluene; Heating;

DOI:10.1021/jm9906264

Reference yield: 79.0%

5-[4-(4-methylphenyl)phenyl]pentanoic acid → 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (229006-86-4)

Guidance literature:

With polyphosphoric acid; at 70 - 105 ℃; for 12h; Large scale;

DOI:10.1021/op000074v

Reference yield:

ethyl glutaroyl chloride (5205-39-0) → 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (229006-86-4)

Guidance literature:

Multi-step reaction with 5 steps

1: AlCl₃ / 3.5 h / 20 °C

2: 2 N aq. NaOH / methanol / 1.5 h / Heating

3: 73 percent / triethylsilane; TFA / 48 h / 55 °C

4: 67 percent / polyphosphoric acid / 12 h / 100 °C

5: 98 percent / tetrakis(triphenylphosphine)palladium; 2 M aq. K₂CO₃ / ethanol; toluene / Heating

With triethylsilane; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; PPA; potassium carbonate; trifluoroacetic acid; In methanol; ethanol; toluene; 1: Friedel-Crafts reaction / 2: Hydrolysis / 3: Reduction / 4: intramolecular Friedel-Crafts reaction / 5: Suzuki coupling;

DOI:10.1021/jm9906264

upstream raw materials:

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

4-methylphenylboronic acid

ethyl glutaroyl chloride

bromobenzene

Downstream raw materials:

3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester

2-[(4-methyl)phenyl]-N-{4-[(piperidin-1-yl)methyl]phenyl}-6,7-dihydro-5H-benzo[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