5-(6-(tert-butyldimethylsilyloxy)hex-1-ynyl)dihydrofuran-2(3H)-one | 1189152-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(6-(tert-butyldimethylsilyloxy)hex-1-ynyl)dihydrofuran-2(3H)-one
• CAS: 1189152-47-3
• 化学式: C₁₆H₂₈O₃Si
• 分子量: 296.482
• InChiKey: NSHUHQYOMHXEJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(6-(tert-butyldimethylsilyloxy)hex-1-ynyl)dihydrofuran-2(3H)-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到5-(6-hydroxyhex-1-ynyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Modeling a Macrocyclic Bis[spirodiepoxide] Strategy to Erythronolide A

  摘要：

  A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

  DOI：

  10.1021/ol901755a
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以62%的产率得到5-(6-(tert-butyldimethylsilyloxy)hex-1-ynyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Modeling a Macrocyclic Bis[spirodiepoxide] Strategy to Erythronolide A

  摘要：

  A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

  DOI：

  10.1021/ol901755a