(2E)-2-[(4-phenylphenyl)methylidene]cyclopropane-1-carbaldehyde | 1206907-17-6

• 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: (2E)-2-[(4-phenylphenyl)methylidene]cyclopropane-1-carbaldehyde
• CAS: 1206907-17-6
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: HXIKSGYVIAFCIT-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-[(4-phenylphenyl)methylidene]cyclopropane-1-carbaldehyde 、 1-(3-氯丙基)-3-环己基脲 以 甲苯 为溶剂， 反应 3.0h， 以32%的产率得到(4-bromophenyl)-[(1S,5R)-4-methylidene-5-(4-phenylphenyl)cyclopent-2-en-1-yl]methanone
  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

• HOTf-Catalyzed Rearrangement of Methylenecyclopropane Aryl and Alkyl Alcohols
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1002/ejoc.201000509

  日期：2010.7

  An efficient method to synthesize multisubstituted naphthalene and cyclobutanol derivatives through ring opening/ring enlargement of readily available methylenecyclopropane diaryl alcohols or dialkyl- and monoalkyl- as well as monoaryl alcohols in moderate to good yields has been described in this paper. The formation of naphthalene derivatives is a sequential reaction involving a cation-induced ring

  本文描述了一种通过容易获得的亚甲基环丙烷二芳醇或二烷基和单烷基以及单芳醇的开环/扩环来合成多取代萘和环丁醇衍生物的有效方法，产率中等至良好。萘衍生物的形成是一个连续反应，包括环丙烷的阳离子诱导开环、Friedel Crafts 烷基化反应，然后是芳构化。另一方面，环丁醇衍生物的生产是一个阳离子诱导的扩环过程。还介绍了范围和限制。
• 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。
• 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.