1-Methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione

Base Information

• Chemical Name: 1-Methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione
• CAS No.: 127791-78-0
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.275
• ChEMBL ID: CHEMBL4206049
• DSSTox Substance ID: DTXSID30562141
• Nikkaji Number: J337.827F
• Pharos Ligand ID: RWCTHX4GZCXY
• Wikidata: Q82446166
• Mol file: 127791-78-0.mol

Synonyms:127791-78-0;1-methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione;1-METHYL-5,6,7,8-TETRAHYDRO-3,4-PHENANTHRENEDIONE;CHEMBL4206049;DTXSID30562141;BDBM50458274

Chemical Property of 1-Methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione

Chemical Property:

• PSA: 34.14000
• LogP: 2.73410
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 226.099379685
• Heavy Atom Count: 17
• Complexity: 394

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(=O)C2=C1C=CC3=C2CCCC3

Technology Process of 1-Methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione

There total 5 articles about 1-Methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione 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: 66.0%

1-vinylcyclohexene (2622-21-1) + 4-methyl-1,2-dihydroxybenzene (452-86-8) → 1-methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione (127791-78-0)

Guidance literature:

With silver(l) oxide; In ethanol; at 24 ℃; for 3h; ultrasonication;

DOI:10.1021/jo00304a010

Reference yield:

3'-methoxy-6-(2-methoxyvinyl)-5'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl → 3-Methyl-5,6,7,8-tetrahydro-phenanthrene-1,2-dione + 1-methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione (127791-78-0)

Guidance literature:

3'-methoxy-6-(2-methoxyvinyl)-5'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl; With methanesulfonic acid; In dichloromethane; at 0 - 20 ℃; for 18h;

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 18h;

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2018.02.052

Reference yield:

1-bromo-2-(2-methoxyvinyl)cyclohexene → 3-Methyl-5,6,7,8-tetrahydro-phenanthrene-1,2-dione + 1-methyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione (127791-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 18 h / Reflux

2.1: methanesulfonic acid / dichloromethane / 18 h / 0 - 20 °C

2.2: 18 h / -78 - 20 °C

2.3: 1 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; caesium carbonate; In tetrahydrofuran; dichloromethane; 1.1: |Suzuki Coupling;

DOI:10.1016/j.ejmech.2018.02.052

upstream raw materials:

1-vinylcyclohexene

4-methyl-1,2-dihydroxybenzene

cyclohexanone

2-bromocyclohex-1-ene-1-carbaldehyde