2-bromo-1-(2-pentyn-4-ol)-cyclopent-2-en-1-ol | 137527-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(2-pentyn-4-ol)-cyclopent-2-en-1-ol
• 英文别名: 2-Bromo-1-(4-hydroxypent-2-ynyl)cyclopent-2-en-1-ol
• CAS: 137527-68-5
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: XAEWXBNEJRRZTK-UHFFFAOYSA-N

物化性质

• 沸点：
  368.9±42.0 °C(Predicted)
• 密度：
  1.550±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(2-pentyn-4-ol)-cyclopent-2-en-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 8.08h， 生成
  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
• 作为产物：
  描述：

  2-环戊烯酮 在 乙基溴化镁 、 溴 、 magnesium 、 三乙胺 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 2-bromo-1-(2-pentyn-4-ol)-cyclopent-2-en-1-ol
  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.