methyl (2Z)-7-hydroxyhept-2-en-4-ynoate | 1111219-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2Z)-7-hydroxyhept-2-en-4-ynoate
• 英文别名: methyl (Z)-7-hydroxyhept-2-en-4-ynoate
• CAS: 1111219-38-5
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: BLSJRNQAADJWNK-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-7-hydroxyhept-2-en-4-ynoate 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以40%的产率得到6-(2-hydroxyethyl)-5-iodo-2H-pyran-2-one
  参考文献：
  名称：

  Biomimetic Synthesis toward the Transtaganolides/Basiliolides

  摘要：

  A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.

  DOI：

  10.1021/ol802760z
• 作为产物：
  描述：

  (Z)-3-碘丙烯酸甲酯 、 3-丁炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到methyl (2Z)-7-hydroxyhept-2-en-4-ynoate
  参考文献：
  名称：

  Progress toward the synthesis of the transtaganolide/basiliolide natural products: an Ireland–Claisen approach

  摘要：

  Efforts toward the synthesis of the transtaganolide natural product family are described. A highly efficient Ireland-Claisen/Diels-Alder approach has been developed, which rapidly constructs the highly oxygenated and stereochemically rich core of these natural products. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2009.01.108

文献信息

• Progress toward the synthesis of the transtaganolide/basiliolide natural products: an Ireland–Claisen approach
  作者：Hosea M. Nelson、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2009.01.108

  日期：2009.4

  Efforts toward the synthesis of the transtaganolide natural product family are described. A highly efficient Ireland-Claisen/Diels-Alder approach has been developed, which rapidly constructs the highly oxygenated and stereochemically rich core of these natural products. (C) 2009 Elsevier Ltd. All rights reserved,
• Biomimetic Synthesis toward the Transtaganolides/Basiliolides
  作者：Rikard Larsson、Olov Sterner、Martin Johansson

  DOI：10.1021/ol802760z

  日期：2009.2.5

  A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.