allyl(chloro)diethoxysilane | 18388-04-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: allyl(chloro)diethoxysilane
• 英文别名: Chloro-diethoxy-prop-2-enylsilane
• CAS: 18388-04-0
• 化学式: C₇H₁₅ClO₂Si
• 分子量: 194.733
• InChiKey: GJEKGFXIZJVEIL-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 16 Torr)
• 密度：
  0.982 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl(chloro)diethoxysilane 、 2-iodoazobenzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以35%的产率得到(E)-allyldiethoxy[2-(phenylazo)phenyl]silane
  参考文献：
  名称：

  通过硅配位数的光开关控制带有 2-(苯基偶氮)苯基的烯丙基硅烷的反应性

  摘要：

  通过 X 射线分析和多核 NMR 光谱证实，烯丙基二氟 [2-(苯基偶氮)苯基]硅烷中硅的配位数在 4 和 5 之间发生光切换，导致多步反应进行或停止，生成四氟 [2-( 1-烯丙基-2-苯基肼基)苯基]硅酸盐而不改变其他反应条件。

  DOI：

  10.1021/ja037404m
• 作为产物：
  描述：

  硅酸四乙酯 、 丙烯基三氯硅烷 在 三苯基膦 作用下， 反应 168.0h， 生成 三乙氧基氯硅烷 、 allyl(chloro)diethoxysilane
  参考文献：
  名称：

  Intramolecular allylation of the azo group of 2-(allylsilyl)azobenzenes and its photocontrol

  摘要：

  Pentacoordinate allylsilanes bearing an azobenzene moiety were synthesized and their structures were elucidated. The reaction of allyldifluorosilane (E)-7a with BF3 center dot OEt2 did not proceed, but (E)-7a was allowed to react with a fluoride ion to give tetrafluorosilicate 8a via intramolecular allyl-migration from the silicon atom onto the azo group. Activation of both the nucleophilic and electrophilic parts by the Si center dot center dot center dot N interaction was found to be important for promotion of the allyl-migration reaction. The azobenzene moiety of the allylsilane was reversibly isomerized by photoirradiation. The (Z)-7a formed by photoirradiation of (E)-7a is in a tetracoordinate state in contrast to the (E)-7a, and it did not react with a fluoride ion at all under the conditions where (E)-7a reacted quantitatively. The reactivity was successfully controlled without changing any conditions other than the change of the coordination number of the silicon atom induced by photoirradiation. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.045

文献信息

• Intramolecular allylation of the azo group of 2-(allylsilyl)azobenzenes and its photocontrol
  作者：Masaki Yamamura、Naokazu Kano、Takayuki Kawashima

  DOI：10.1016/j.jorganchem.2006.08.045

  日期：2007.1

  Pentacoordinate allylsilanes bearing an azobenzene moiety were synthesized and their structures were elucidated. The reaction of allyldifluorosilane (E)-7a with BF3 center dot OEt2 did not proceed, but (E)-7a was allowed to react with a fluoride ion to give tetrafluorosilicate 8a via intramolecular allyl-migration from the silicon atom onto the azo group. Activation of both the nucleophilic and electrophilic parts by the Si center dot center dot center dot N interaction was found to be important for promotion of the allyl-migration reaction. The azobenzene moiety of the allylsilane was reversibly isomerized by photoirradiation. The (Z)-7a formed by photoirradiation of (E)-7a is in a tetracoordinate state in contrast to the (E)-7a, and it did not react with a fluoride ion at all under the conditions where (E)-7a reacted quantitatively. The reactivity was successfully controlled without changing any conditions other than the change of the coordination number of the silicon atom induced by photoirradiation. (c) 2006 Elsevier B.V. All rights reserved.
• Reactivity Control of an Allylsilane Bearing a 2-(Phenylazo)phenyl Group by Photoswitching of the Coordination Number of Silicon
  作者：Naokazu Kano、Masaki Yamamura、Takayuki Kawashima

  DOI：10.1021/ja037404m

  日期：2004.5.1

  Photoswitching of the coordination number of silicon between four and five in allyldifluoro[2-(phenylazo)phenyl]silane, which was confirmed by X-ray analysis and multinuclear NMR spectroscopy, caused multistep reactions to proceed or stop, yielding tetrafluoro[2-(1-allyl-2-phenylhydrazino)phenyl]silicate without altering other reaction conditions.

  通过 X 射线分析和多核 NMR 光谱证实，烯丙基二氟 [2-(苯基偶氮)苯基]硅烷中硅的配位数在 4 和 5 之间发生光切换，导致多步反应进行或停止，生成四氟 [2-( 1-烯丙基-2-苯基肼基)苯基]硅酸盐而不改变其他反应条件。