2-methoxy-5-(3',4'-methylenedioxyphenyl)cyclohepta-2,4,6-trien-1-one | 134952-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-methoxy-5-(3',4'-methylenedioxyphenyl)cyclohepta-2,4,6-trien-1-one
• 英文别名: 5-(1,3-Benzodioxol-5-yl)-2-methoxycyclohepta-2,4,6-trien-1-one
• CAS: 134952-85-5
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: POISPALLWBHUJN-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  trimethyl(3,4-methylenedioxyphenyl)stannane 在 bis-triphenylphosphine-palladium(II) chloride potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 7.0h， 生成 2-methoxy-5-(3',4'-methylenedioxyphenyl)cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Banwell, Martin G.; Cameron, Jennifer M.; Collis, Maree P., Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 705 - 728

  摘要：

  DOI：

文献信息

• Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology
  作者：W. Michael Seganish、Christopher J. Handy、Philip DeShong

  DOI：10.1021/jo051636h

  日期：2005.10.1

  Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.
• BANWELL, MARTIN G.;CAMERON, JENNIFER M.;COLLIS, MAREE P.;CRISP, GEOFFREY +, AUSTRAL. J. CHEM., 44,(1991) N, C. 705-728
  作者：BANWELL, MARTIN G.、CAMERON, JENNIFER M.、COLLIS, MAREE P.、CRISP, GEOFFREY +

  DOI：——

  日期：——