(E)-1-(4-trimethylsilyl-1-buten-3-ynyl)-8-(trimethylsilylethynyl)naphthalene | 205124-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-1-(4-trimethylsilyl-1-buten-3-ynyl)-8-(trimethylsilylethynyl)naphthalene
• 英文别名: trimethyl-[2-[8-[(E)-4-trimethylsilylbut-1-en-3-ynyl]naphthalen-1-yl]ethynyl]silane
• CAS: 205124-47-6
• 化学式: C₂₂H₂₆Si₂
• 分子量: 346.619
• InChiKey: RDZXANRUKZWBOJ-YRNVUSSQSA-N

物化性质

• 沸点：
  429.2±38.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-trimethylsilyl-1-buten-3-ynyl)-8-(trimethylsilylethynyl)naphthalene 在 四丁基氟化铵 、 对苯二酚 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 10.0h， 生成 荧蒽
  参考文献：
  名称：

  Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes

  摘要：

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

  DOI：

  10.1021/jo9717853
• 作为产物：
  描述：

  1,8-二碘萘 在 四(三苯基膦)钯 、 tris-(dibenzylideneacetone)dipalladium(0) 哌啶 、 copper(l) iodide 、 三苯胂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 28.0h， 生成 (E)-1-(4-trimethylsilyl-1-buten-3-ynyl)-8-(trimethylsilylethynyl)naphthalene
  参考文献：
  名称：

  Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes

  摘要：

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

  DOI：

  10.1021/jo9717853

文献信息

• Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes
  作者：Juan J. González、Andrés Francesch、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1021/jo9717853

  日期：1998.5.1

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.