5-(9-(tert-butyldimethylsilyloxy)-6-hydroxynona-1,7-diynyl)dihydrofuran-2(3H)-one | 1189152-40-6

• 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-(9-(tert-butyldimethylsilyloxy)-6-hydroxynona-1,7-diynyl)dihydrofuran-2(3H)-one
• CAS: 1189152-40-6
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: KFBASSJPEPLHMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(9-(tert-butyldimethylsilyloxy)-6-hydroxynona-1,7-diynyl)dihydrofuran-2(3H)-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成
  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：

  6-(5-oxotetrahydrofuran-2-yl)hex-5-ynal 、 叔丁基二甲基(2-丙炔氧基)硅烷 在 正丁基锂 、 三异丙氧基氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到5-(9-(tert-butyldimethylsilyloxy)-6-hydroxynona-1,7-diynyl)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