1-{2-[5-(benzhydryloxy)penta-1,3-diyn-1-yl]phenyl}-3-(trimethylsilyl)prop-2-yn-1-ol

• 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: 1-{2-[5-(benzhydryloxy)penta-1,3-diyn-1-yl]phenyl}-3-(trimethylsilyl)prop-2-yn-1-ol
• 英文别名: 1-[2-[5-[(4-Methoxyphenyl)-phenylmethoxy]penta-1,3-diynyl]phenyl]-3-trimethylsilylprop-2-yn-1-ol；1-[2-[5-[(4-methoxyphenyl)-phenylmethoxy]penta-1,3-diynyl]phenyl]-3-trimethylsilylprop-2-yn-1-ol
• 化学式: C₃₁H₃₀O₃Si
• 分子量: 478.663
• InChiKey: NDVHJOKGVPKROD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{2-[5-(benzhydryloxy)penta-1,3-diyn-1-yl]phenyl}-3-(trimethylsilyl)prop-2-yn-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到1-{2-[5-(benzhydryloxy)penta-1,3-diyn-1-yl]phenyl}-3-(trimethylsilyl)prop-2-yn-1-one
  参考文献：
  名称：

  Intramolecular [4 + 2] Trapping of a Hexadehydro-Diels–Alder (HDDA) Benzyne by Tethered Arenes

  摘要：

  We report here the efficient, intramolecular trapping in a Diels-Alder (DA) sense of thermally generated benzynes by one of two pendant arene rings. A more electron-rich ring (p-methoxyphenyl) reacted substantially faster than a simple phenyl ring, which was, in turn, slightly more reactive vs a 4-carbomethoxyphenyl ring. Photoinduced di-pi-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.

  DOI：

  10.1021/ol5037024
• 作为产物：
  描述：

  4-甲氧基二苯甲醇 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 silver nitrate 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 6.83h， 生成 1-{2-[5-(benzhydryloxy)penta-1,3-diyn-1-yl]phenyl}-3-(trimethylsilyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Intramolecular [4 + 2] Trapping of a Hexadehydro-Diels–Alder (HDDA) Benzyne by Tethered Arenes

  摘要：

  We report here the efficient, intramolecular trapping in a Diels-Alder (DA) sense of thermally generated benzynes by one of two pendant arene rings. A more electron-rich ring (p-methoxyphenyl) reacted substantially faster than a simple phenyl ring, which was, in turn, slightly more reactive vs a 4-carbomethoxyphenyl ring. Photoinduced di-pi-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.

  DOI：

  10.1021/ol5037024

文献信息

• Intramolecular [4 + 2] Trapping of a Hexadehydro-Diels–Alder (HDDA) Benzyne by Tethered Arenes
  作者：Vedamayee D. Pogula、Tao Wang、Thomas R. Hoye

  DOI：10.1021/ol5037024

  日期：2015.2.20

  We report here the efficient, intramolecular trapping in a Diels-Alder (DA) sense of thermally generated benzynes by one of two pendant arene rings. A more electron-rich ring (p-methoxyphenyl) reacted substantially faster than a simple phenyl ring, which was, in turn, slightly more reactive vs a 4-carbomethoxyphenyl ring. Photoinduced di-pi-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.