6-(5-oxotetrahydrofuran-2-yl)hex-5-ynal | 1189152-48-4

• 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: 6-(5-oxotetrahydrofuran-2-yl)hex-5-ynal
• 英文别名: 6-(5-Oxooxolan-2-yl)hex-5-ynal；6-(5-oxooxolan-2-yl)hex-5-ynal
• CAS: 1189152-48-4
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: SCZFIWXINPOJPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-(6-hydroxyhex-1-ynyl)dihydrofuran-2(3H)-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以91%的产率得到6-(5-oxotetrahydrofuran-2-yl)hex-5-ynal
  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

文献信息

• Modeling a Macrocyclic Bis[spirodiepoxide] Strategy to Erythronolide A
  作者：Partha Ghosh、Yue Zhang、Thomas J. Emge、Lawrence J. Williams

  DOI：10.1021/ol901755a

  日期：2009.10.1

  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.