2-(1-(4-((trimethylsilyl)ethynyl)phenyl)ethylidene)malononitrile | 1401464-91-2

• 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: 2-(1-(4-((trimethylsilyl)ethynyl)phenyl)ethylidene)malononitrile
• 英文别名: 2-[1-[4-(2-Trimethylsilylethynyl)phenyl]ethylidene]propanedinitrile；2-[1-[4-(2-trimethylsilylethynyl)phenyl]ethylidene]propanedinitrile
• CAS: 1401464-91-2
• 化学式: C₁₆H₁₆N₂Si
• 分子量: 264.402
• InChiKey: LKWLTVMKOLENGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-(4-((trimethylsilyl)ethynyl)phenyl)ethylidene)malononitrile 在 四丁基氟化铵 、 trityl tetrafluoroborate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.25h， 生成 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile
  参考文献：
  名称：

  多态开关：炔烷基-二氢杂氮烯/乙烯基庚七烯共轭物

  摘要：

  包含独特且可独立寻址的功能组件的多模分子开关具有潜在的应用，如分子电子和存储器存储设备的高级开关和逻辑门。在本文中，我们描述了基于以二氢氮杂烯/乙烯基庚二烯（DHA / VHF）光电/热开关对为基础的四个开关的合成和表征，该对基于钌的Cp *（dppe）Ru（[Ru *]）金属配合物（dppe = 1 ，2-双（二苯基膦基）乙烷； Cp * ＝五甲基环戊二烯基）。[Ru *] – DHA共轭物可能以六种不同状态存在，可通过DHA / VHF，Ru II / Ru III之间的交替访问和炔基/亚乙烯基，可以通过使用光/热，氧化/还原和酸/碱分别进行刺激。发现在这些[Ru *]-DHA共轭物中，进入所有状态的过程很大程度上取决于金属中心与有机光电开关之间的电子通信。详细的电化学，光谱学（UV / Vis，IR，NMR）和X射线晶体学研究确实揭示了两个部分之间的重要电子相互作用。在直接结合时，发

  DOI：

  10.1002/chem.201600178
• 作为产物：
  描述：

  4'-(2-trimethylsilylethynyl)acetophenone 、 丙二腈 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到2-(1-(4-((trimethylsilyl)ethynyl)phenyl)ethylidene)malononitrile
  参考文献：
  名称：

  Dihydroazulene–Buckminsterfullerene Conjugates

  摘要：

  The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit

  DOI：

  10.1021/jo301306y

文献信息

• Dihydroazulene–Buckminsterfullerene Conjugates
  作者：Marco Santella、Virginia Mazzanti、Martyn Jevric、Christian Richard Parker、Søren Lindbæk Broman、Andrew D. Bond、Mogens Brøndsted Nielsen

  DOI：10.1021/jo301306y

  日期：2012.10.19

  The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit
• Multistate Switches: Ruthenium Alkynyl–Dihydroazulene/Vinylheptafulvene Conjugates
  作者：Alexandru Vlasceanu、Cecilie L. Andersen、Christian R. Parker、Ole Hammerich、Thorbjørn J. Morsing、Martyn Jevric、Søren Lindbæk Broman、Anders Kadziola、Mogens Brøndsted Nielsen

  DOI：10.1002/chem.201600178

  日期：2016.5.23

  dependent on the electronic communication between the metal center and the organic photoswitch in these [Ru*]–DHA conjugates. Detailed electrochemical, spectroscopic (UV/Vis, IR, NMR), and X‐ray crystallographic studies indeed reveal significant electronic interactions between the two moieties. When in direct conjugation, the ruthenium metal center was found to quench the photochemical ring‐opening of

  包含独特且可独立寻址的功能组件的多模分子开关具有潜在的应用，如分子电子和存储器存储设备的高级开关和逻辑门。在本文中，我们描述了基于以二氢氮杂烯/乙烯基庚二烯（DHA / VHF）光电/热开关对为基础的四个开关的合成和表征，该对基于钌的Cp *（dppe）Ru（[Ru *]）金属配合物（dppe = 1 ，2-双（二苯基膦基）乙烷； Cp * ＝五甲基环戊二烯基）。[Ru *] – DHA共轭物可能以六种不同状态存在，可通过DHA / VHF，Ru II / Ru III之间的交替访问和炔基/亚乙烯基，可以通过使用光/热，氧化/还原和酸/碱分别进行刺激。发现在这些[Ru *]-DHA共轭物中，进入所有状态的过程很大程度上取决于金属中心与有机光电开关之间的电子通信。详细的电化学，光谱学（UV / Vis，IR，NMR）和X射线晶体学研究确实揭示了两个部分之间的重要电子相互作用。在直接结合时，发