(2E)-2-[(3,4-dimethylphenyl)methylidene]cyclopropane-1-carbaldehyde | 1258399-39-1

• 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: (2E)-2-[(3,4-dimethylphenyl)methylidene]cyclopropane-1-carbaldehyde
• CAS: 1258399-39-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: IKHSHRPBQNLILO-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (2E)-2-[(3,4-dimethylphenyl)methylidene]cyclopropane-1-carbaldehyde 、 1-三苯基膦-2-丙酮 以 二氯甲烷 为溶剂， 生成
  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：

  在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 (2E)-2-[(3,4-dimethylphenyl)methylidene]cyclopropane-1-carbaldehyde
  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

• Ring-Opening Reaction of Methylenecyclopropanes Derived from Methylenecyclopropyl Aldehydes through Cope Rearrangement
  作者：Xiang-Ying Tang、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201000880

  日期：2010.11

  Tandem Wittig reaction/Cope rearrangement of methylenecyclopropyl aldehydes 1 with cinnamyltriphenylphosphonium bromide afforded a convenient method for the synthesis of cyclopentene derivatives 2 in moderate yields in a one-pot manner. Dialkyl 2-[(2-methylenecyclopropyl)methylene]malonates 3 derived from methylenecyclopropyl aldehydes 1 could produce two kinds of cyclopentene derivatives, 4 and 5

  亚甲基环丙醛 1 与肉桂基三苯基溴化鏻的串联 Wittig 反应/Cope 重排为以一锅法以中等产率合成环戊烯衍生物 2 提供了一种方便的方法。衍生自亚甲基环丙基醛 1 的二烷基 2-[(2-亚甲基环丙基) 亚甲基]丙二酸酯 3 可以通过在 100 摄氏度加热时通过热诱导 Cope 重排产生两种环戊烯衍生物 4 和 5，总产率良好。 合理的反应机制在以前的报告和对照实验的基础上进行了讨论。