(Z)-2-prop-2-enyl-5-trimethylsilylpent-2-en-4-ynal | 607731-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-2-prop-2-enyl-5-trimethylsilylpent-2-en-4-ynal
• CAS: 607731-37-3
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: KTUGBSOAEDQENJ-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-prop-2-enyl-5-trimethylsilylpent-2-en-4-ynal 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 methyl (2E,4Z)-4-prop-2-enylhepta-2,4-dien-6-ynoate
  参考文献：
  名称：

  Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol

  摘要：

  The reaction of various carbene complexes with dienylacetylenes has been examined. The reaction has been used as the cornerstone for the preparation of the nor-neolignan natural product egonol in five steps from readily available components. In most examples of the carbene-alkyne coupling, the reaction proceeds to form benzofuran derivatives. In the case of one highly functionalized terminal alkyne, a competing rearrangement/cyclization process occurs in preference to the carbene coupling process. The use of silylated alkynes subverts this process. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00823-8
• 作为产物：
  描述：

  (Z)-2-(2-propen-1-yl)-5-trimethylsilyl-2-penten-4-yn-1-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(Z)-2-prop-2-enyl-5-trimethylsilylpent-2-en-4-ynal
  参考文献：
  名称：

  Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol

  摘要：

  The reaction of various carbene complexes with dienylacetylenes has been examined. The reaction has been used as the cornerstone for the preparation of the nor-neolignan natural product egonol in five steps from readily available components. In most examples of the carbene-alkyne coupling, the reaction proceeds to form benzofuran derivatives. In the case of one highly functionalized terminal alkyne, a competing rearrangement/cyclization process occurs in preference to the carbene coupling process. The use of silylated alkynes subverts this process. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00823-8

文献信息

• Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol
  作者：Jianwei Zhang、Yi Zhang、Yanshi Zhang、James W Herndon

  DOI：10.1016/s0040-4020(03)00823-8

  日期：2003.7

  The reaction of various carbene complexes with dienylacetylenes has been examined. The reaction has been used as the cornerstone for the preparation of the nor-neolignan natural product egonol in five steps from readily available components. In most examples of the carbene-alkyne coupling, the reaction proceeds to form benzofuran derivatives. In the case of one highly functionalized terminal alkyne, a competing rearrangement/cyclization process occurs in preference to the carbene coupling process. The use of silylated alkynes subverts this process. (C) 2003 Elsevier Science Ltd. All rights reserved.