3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one

Base Information

• Chemical Name: 3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one
• CAS No.: 22725-38-8
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.27
• DSSTox Substance ID: DTXSID10575991
• Mol file: 22725-38-8.mol

Synonyms:3-Methoxy 5-Dibenzosuberenone;22725-38-8;3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one;5-methoxytricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-one;SCHEMBL5334950;DTXSID10575991

Chemical Property of 3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one

Chemical Property:

• Melting Point: 69-71oC
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 236.083729621
• Heavy Atom Count: 18
• Complexity: 347

Purity/Quality:

97% ^*data from raw suppliers

3-Methoxy5-Dibenzosuberenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC2=C(C=CC3=CC=CC=C3C2=O)C=C1
• Uses: An intermediate in the preparation of pharmaceutically active Cyproheptadines.

Technology Process of 3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one

There total 10 articles about 3-Methoxy-5H-dibenzo[a,d][7]annulen-5-one 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:

3-Methoxy-dibenzo<1,4>cycloheptadien-5-on (17910-76-8) → 3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one (22725-38-8)

Guidance literature:

10,11-dihydro-3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one; With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; for 3h; Heating / reflux;

With triethylamine; In 1,2-dichloro-ethane; for 2h; Heating / reflux;

Reference yield:

C16H13ClO2 → 3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one (22725-38-8)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/acs.jmedchem.1c00979

Reference yield:

2-Methyl-benzoic acid methyl ester (89-71-4) → 3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one (22725-38-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 1 h / 70 °C

2.1: triphenylphosphine / acetone / 1 h / Reflux

2.2: 6 h / Reflux

3.1: potassium hydroxide; water / methanol / 4 h / Reflux

4.1: thionyl chloride / dichloromethane / 1.5 h / Reflux

5.1: aluminum (III) chloride / dichloromethane / 3 h / 20 °C

With aluminum (III) chloride; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); water; triphenylphosphine; potassium hydroxide; In methanol; dichloromethane; chlorobenzene; acetone; 5.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.jmedchem.1c00979

upstream raw materials:

3-Methoxy-dibenzo<1,4>cycloheptadien-5-on

2-Methyl-benzoic acid methyl ester

4'-methylstilbene-2-carboxylic acid

methyl 2-bromomethylbenzoate

Downstream raw materials:

3-hydroxy-5H-dibenzo[a,d]cyclohepten-5-one

4-(3-methoxy-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-piperidine