2-[4-(triisopropylsilylethynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile | 1401464-89-8

• 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-[4-(triisopropylsilylethynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile
• 英文别名: 2-[4-[2-tri(propan-2-yl)silylethynyl]phenyl]-8aH-azulene-1,1-dicarbonitrile
• CAS: 1401464-89-8
• 化学式: C₂₉H₃₂N₂Si
• 分子量: 436.672
• InChiKey: JZNLVWNMODMVBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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-[4-(triisopropylsilylethynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以76%的产率得到2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile
  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
• 作为产物：
  描述：

  以 乙腈 为溶剂， 生成 2-[4-(triisopropylsilylethynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile
  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

• Syntheses of Donor–Acceptor-Functionalized Dihydroazulenes
  作者：Søren Lindbæk Broman、Martyn Jevric、Andrew D. Bond、Mogens Brøndsted Nielsen

  DOI：10.1021/jo4020326

  日期：2014.1.3

  properties relies on ready access to new derivatives via efficient synthetic protocols. The central DHA core is conveniently prepared in a four-step synthesis starting from acetophenone and tropylium substrates. Here, the outcome of this reaction as a function of the nature of the substituent group on the phenyl unit of acetophenone is investigated in detail. A wide variety of functional groups (nitro, cyano

  二氢氮杂烯（DHA）/乙烯基庚二烯（VHF）光电/热敏开关已被广泛用于分子电子学和高级材料中。先前已经发现两种异构体之间的转换很大程度上取决于供体和受体基团的存在。光学和开关特性的微调取决于通过有效的合成协议对新衍生物的便捷访问。中心DHA核心可方便地以四步合成的方式从苯乙酮和对苯二铵底物开始制备。在此，根据苯乙酮的苯基单元上的取代基的性质，对该反应的结果进行了详细研究。可以耐受多种官能团（硝基，氰基，卤素，烷基，酰胺基和硫醚），并且该路线为人们提供了更多选择的DHA衍生物（DHA的位置2）。通过区域选择性溴化-消除方案研究了这些化合物在七元环中随后进行官能化的能力，并在位置7引入了溴取代基。对卤代DHA进行了钯催化的氰化反应，Sonogashira，Cadiot-Chodkiewicz ，铃木联轴器以及后者的反应；通过改变钯催化剂开发了最佳条件。总的来说，我们的重点是减少完全不饱和的z烯