2-Methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-one

Base Information

• Chemical Name: 2-Methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-one
• CAS No.: 118062-06-9
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.274
• DSSTox Substance ID: DTXSID101198083
• Mol file: 118062-06-9.mol

Synonyms:2-methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-one;DTXSID101198083;118062-06-9;2-methoxy-5-(2-methoxyphenyl)-cyclohepta-2,4,6-trien-1-one

Chemical Property of 2-Methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-one

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 404

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC=C1C2=CC=C(C(=O)C=C2)OC

Technology Process of 2-Methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-one

There total 5 articles about 2-Methoxy-5-(2-methoxyphenyl)-2,4,6-cycloheptatrien-1-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: 71.0%

5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one (33816-51-2) + 2-Methoxyphenylboronic acid (5720-06-9) → 2-methoxy-5-(2'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one (118062-06-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; benzene; for 18h; Heating;

Reference yield:

5-bromotropolone (3172-00-7) → 2-methoxy-5-(2'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one (118062-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / H₂O; acetone / 4 h / Heating

2: 194 mg / Na₂CO₃ / Pd(PPh₃)4 / toluene; ethanol / 5 h / Heating

With sodium carbonate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; acetone; toluene; 2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/jo051636h

Reference yield:

2-bromoanisole (578-57-4) → 2-methoxy-5-(2'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one (118062-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / tetrahydrofuran / 3 h / Heating

1.2: trimethyl borate / tetrahydrofuran / -78 - 20 °C

1.3: HCl / tetrahydrofuran; H₂O

2.1: 194 mg / Na₂CO₃ / Pd(PPh₃)4 / toluene; ethanol / 5 h / Heating

With sodium carbonate; magnesium; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; toluene; 2.1: Suzuki-Miyaura cross-coupling;

DOI:10.1021/jo051636h

upstream raw materials:

5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one

2-Methoxyphenylboronic acid

dimethyl sulfate

2-bromoanisole

Refernces

• 1、 Banwell, Martin G.,Cameron, Jennifer M.,Collis, Maree P.,Crisp, Geoffrey T.,Gable, Robert W.,'et al.. "The Palladium-Mediated Cross Coupling of Bromotropolones with Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogues". . p. 705 - 728. Retrieved 2007/10/02.