E-1-(ethynyl)-5-(4-oxo-2-pentynylidene)cyclopentene | 137527-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: E-1-(ethynyl)-5-(4-oxo-2-pentynylidene)cyclopentene
• 英文别名: (5E)-5-(2-ethynylcyclopent-2-en-1-ylidene)pent-3-yn-2-one
• CAS: 137527-67-4
• 化学式: C₁₂H₁₀O
• 分子量: 170.211
• InChiKey: HYXKBVLKVJWNAT-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-1-(ethynyl)-5-(4-oxo-2-pentynylidene)cyclopentene 在 氧气 作用下， 以 氘代氯仿 为溶剂， 反应 133.0h， 以42%的产率得到5-[1-Ethynyl-6-oxa-bicyclo[3.1.0]hex-(2E)-ylidene]-pent-3-yn-2-one
  参考文献：
  名称：

  Reactions of Neocarzinostatin Chromophore Analogues with Molecular Oxygen

  摘要：

  交错共轭的5-亚甲基-3-庚烯-1,6-二炔衍生物已被证明可以被分子氧容易地环氧化。

  DOI：

  10.1246/cl.1994.457
• 作为产物：
  描述：

  2-溴-2-环戊酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 乙基溴化镁 、 potassium carbonate 、 magnesium 、 二甲基亚砜 、 三乙胺 、 二异丙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 E-1-(ethynyl)-5-(4-oxo-2-pentynylidene)cyclopentene
  参考文献：
  名称：

  The synthesis and chemistry of a simplified, functional analogue of neocarzinostatin chromophore: identification of an intramolecular 1,5-hydrogen atom

  摘要：

  The synthesis and chemistry of a monocyclic analogue of neocarzinostatin chromophore are described. This analogue is activated through a Michael addition process and provides cycloaromatized products similar to those obtained in the activation of neocarzinostatin chromophore. Mechanistic studies on this analogue have led to the first identification of a diyl self-quenching pathway based on a 1,5-hydrogen atom transfer that provides a novel hypothesis about the relationship between thiol structure and DNA single and double strand cleavage selectivity for neocarzinostatin chromophore and diyl-based cleaving agents.

  DOI：

  10.1016/s0040-4020(01)80627-x
• 作为试剂：
  描述：

  beta-pinene 、 巯基乙酸甲酯 在 E-1-(ethynyl)-5-(4-oxo-2-pentynylidene)cyclopentene 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以2.1%的产率得到
  参考文献：
  名称：

  The synthesis and chemistry of a simplified, functional analogue of neocarzinostatin chromophore: identification of an intramolecular 1,5-hydrogen atom

  摘要：

  The synthesis and chemistry of a monocyclic analogue of neocarzinostatin chromophore are described. This analogue is activated through a Michael addition process and provides cycloaromatized products similar to those obtained in the activation of neocarzinostatin chromophore. Mechanistic studies on this analogue have led to the first identification of a diyl self-quenching pathway based on a 1,5-hydrogen atom transfer that provides a novel hypothesis about the relationship between thiol structure and DNA single and double strand cleavage selectivity for neocarzinostatin chromophore and diyl-based cleaving agents.

  DOI：

  10.1016/s0040-4020(01)80627-x

文献信息

• Studies on DNA cleaving agents: synthesis and chemically induced cycloaromatization of a monocyclic neocarzinostatin chromophore analogue
  作者：Paul A. Wender、Mark J. Tebbe

  DOI：10.1016/s0040-4039(00)93481-6

  日期：1991.9

  The synthesis of an acyclic analogue of neocarzinostatin chromophore is described. This analogue is found to undergo cycloaromatization in the presence of thiols; the process involves a previously undetected internal hydrogen abstraction reaction.