(E)-4-((Z)-2-benzylidenecyclopropyl)but-3-en-2-one | 1206906-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-((Z)-2-benzylidenecyclopropyl)but-3-en-2-one
• 英文别名: (E)-4-[(2Z)-2-benzylidenecyclopropyl]but-3-en-2-one
• CAS: 1206906-94-6
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: HQTUUUFQPWBSPR-ZHCWNNSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-4-((Z)-2-benzylidenecyclopropyl)but-3-en-2-one 以 甲苯 为溶剂， 反应 1.0h， 以70%的产率得到1-(4-methylene-5-phenylcyclopent-2-enyl)ethanone
  参考文献：
  名称：

  A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives

  摘要：

  A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.

  DOI：

  10.1021/jo902512q
• 作为产物：
  描述：

  (Z)-2-benzylidenecyclopropanecarbaldehyde 、 1-三苯基膦-2-丙酮 以 二氯甲烷 为溶剂， 生成 (E)-4-((Z)-2-benzylidenecyclopropyl)but-3-en-2-one
  参考文献：
  名称：

  A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives

  摘要：

  A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.

  DOI：

  10.1021/jo902512q

文献信息

• A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo902512q

  日期：2010.2.5

  A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.