velloziolide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: velloziolide
• 英文别名: 4-ethenyl-11-hydroxy-4,6,10,10-tetramethyl-5,7,8,9-tetrahydro-3H-benzo[h][1]benzoxepin-2-one
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: IDTJPDQPPZBFSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  11-(chloromethoxy)-4-ethenyl-4,6,10,10-tetramethyl-5,7,8,9-tetrahydro-3H-benzo[h][1]benzoxepin-2-one 在 水 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以0.0292 g的产率得到velloziolide
  参考文献：
  名称：

  The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations

  摘要：

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.

  DOI：

  10.1021/jo901471b