Methyl 4-(1,1-dicyano-3-cyclohepta-2,4,6-trien-1-ylprop-1-en-2-yl)benzoate | 1401464-81-0

• 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: Methyl 4-(1,1-dicyano-3-cyclohepta-2,4,6-trien-1-ylprop-1-en-2-yl)benzoate
• 英文别名: methyl 4-(1,1-dicyano-3-cyclohepta-2,4,6-trien-1-ylprop-1-en-2-yl)benzoate
• CAS: 1401464-81-0
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: RPHWCUZHJVEUMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-(1,1-dicyanoprop-1-en-2-yl)benzoate 、 tropylium tetrafluoroborate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 4-(1,1-dicyano-3-cyclohepta-2,4,6-trien-1-ylprop-1-en-2-yl)benzoate 、 Methyl 4-[1,1-dicyano-3,3-di(cyclohepta-2,4,6-trien-1-yl)prop-1-en-2-yl]benzoate 、 环庚三烯
  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