2,2-dimethyl-5-[(1E,3E)-6-trimethylsilylhexa-1,3-dien-5-ynyl]-1,3-benzodioxin-4-one | 1191384-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2,2-dimethyl-5-[(1E,3E)-6-trimethylsilylhexa-1,3-dien-5-ynyl]-1,3-benzodioxin-4-one
• CAS: 1191384-88-9
• 化学式: C₁₉H₂₂O₃Si
• 分子量: 326.467
• InChiKey: NBDMFKKCXHYJJZ-HRCSPUOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propenal 、 (3-三甲基硅基-2-丙炔基)三苯基溴化磷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 、 2,2-dimethyl-5-[(1E,3E)-6-trimethylsilylhexa-1,3-dien-5-ynyl]-1,3-benzodioxin-4-one
  参考文献：
  名称：

  Synthesis of the Monomeric Counterpart of Marinomycin A

  摘要：

  An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.

  DOI：

  10.1021/jo900945x

文献信息

• Synthesis of the Monomeric Counterpart of Marinomycin A
  作者：Dominique Amans、Laurianne Bareille、Véronique Bellosta、Janine Cossy

  DOI：10.1021/jo900945x

  日期：2009.10.16

  An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.