4-(dicyanomethyl)benzaldehyde | 143662-73-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(dicyanomethyl)benzaldehyde
• 英文别名: 4-(dicyanomethyl)-benzaldehyde；2-(4-formylphenyl)propanedinitrile
• CAS: 143662-73-1
• 化学式: C₁₀H₆N₂O
• 分子量: 170.17
• InChiKey: GQGFWALRHPXDNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dicyanomethyl)benzaldehyde 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 7.0h， 生成 [4-[bis(2-oxo-2H-cyclohepta[b]furan-3-yl)methyl]-2,5-cyclohexadiene-1,4-diylidene]propanedinitrile
  参考文献：
  名称：

  Synthesis and properties of 7,7-bis(heteroazulen-3-yl)-8,8-dicyano-1,4-quinodimethanes

  摘要：

  The synthesis and properties of a novel type of 7,7-bis(heteroazulen-3-yl)-8,8-dicyano-1,4-quinodimethanes (9a-c) are studied. The synthetic method is based on a TFA-catalyzed electrophilic aromatic substitution on the heteroazulenes with 4-(dicyanomethyl)benzaldehyde to afford the corresponding methane derivatives, followed by oxidative hydrogen abstraction with DDQ. The polarization of 9a-c is evaluated by the inspection of their C-13 NMR and IR spectra. Based on the investigation of the UV-Vis spectra of 9a-c and protonated cations 10a-c, conformational changes of the heteroazulene-moiety and (dicyanomethyl)phenyl group are suggested. In the CV measurements of 9a-c, two reversible reduction waves are observed, indicating the stabilizing ability of heteroazulenes toward the corresponding radical and anion species. Furthermore, 9a-c exhibit two irreversible oxidation waves, which suggest a conformational change in the radical cation during the redox process. The conformational change is rationalized on the basis of the MO calculations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.031
• 作为产物：
  描述：

  sodium;hydride 、 丙二腈 、 、 4-碘苯甲醛 、 在 氩 、 乙醚 、 4-(dicyanomethyl)benzaldehyde 作用下， 以 乙腈 为溶剂， 反应 66.0h， 生成 4-(dicyanomethyl)benzaldehyde
  参考文献：
  名称：

  Electroactive compounds, compositions and devices and methods of making

  摘要：

  本发明涉及一种电活性化合物，该化合物能够在施加电场下发生光吸收和折射变化，并在暴露于预定光辐射波段下发生永久折射变化。本发明还涉及包含这种电活性化合物的电活性组合物，由这种电活性组合物组成的电光组件和由这种电光组件组成的电光设备，以及制造这些物品的新型工艺。

  公开号：

  US05334333A1
• 作为试剂：
  描述：

  sodium;hydride 、 丙二腈 、 、 4-碘苯甲醛 、 在 氩 、 乙醚 、 4-(dicyanomethyl)benzaldehyde 作用下， 以 乙腈 为溶剂， 反应 66.0h， 生成 4-(dicyanomethyl)benzaldehyde
  参考文献：
  名称：

  Electroactive compounds, compositions and devices and methods of making

  摘要：

  本发明涉及一种电活性化合物，该化合物能够在施加电场下发生光吸收和折射变化，并在暴露于预定光辐射波段下发生永久折射变化。本发明还涉及包含这种电活性化合物的电活性组合物，由这种电活性组合物组成的电光组件和由这种电光组件组成的电光设备，以及制造这些物品的新型工艺。

  公开号：

  US05334333A1

文献信息

• Electroactive compounds, compositions and devices and methods of making the same
  申请人：ATOCHEM NORTH AMERICA, INC.

  公开号：EP0491364A2

  公开（公告）日：1992-06-24

  The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices

  本发明涉及能够因外加电场而改变光吸收和折射以及因暴露于预定波段的光辐射而永久改变折射的电活性化合物。本发明还涉及含有这种电活性化合物的电活性组合物、由这种电活性组合物组成的光电元件和光电设备。
• US5334333A
  申请人：——

  公开号：US5334333A

  公开（公告）日：1994-08-02
• Synthesis and properties of 7,7-bis(heteroazulen-3-yl)-8,8-dicyano-1,4-quinodimethanes
  作者：Shin-ichi Naya、Kyosuke Yoda、Makoto Nitta

  DOI：10.1016/j.tet.2004.04.031

  日期：2004.5

  The synthesis and properties of a novel type of 7,7-bis(heteroazulen-3-yl)-8,8-dicyano-1,4-quinodimethanes (9a-c) are studied. The synthetic method is based on a TFA-catalyzed electrophilic aromatic substitution on the heteroazulenes with 4-(dicyanomethyl)benzaldehyde to afford the corresponding methane derivatives, followed by oxidative hydrogen abstraction with DDQ. The polarization of 9a-c is evaluated by the inspection of their C-13 NMR and IR spectra. Based on the investigation of the UV-Vis spectra of 9a-c and protonated cations 10a-c, conformational changes of the heteroazulene-moiety and (dicyanomethyl)phenyl group are suggested. In the CV measurements of 9a-c, two reversible reduction waves are observed, indicating the stabilizing ability of heteroazulenes toward the corresponding radical and anion species. Furthermore, 9a-c exhibit two irreversible oxidation waves, which suggest a conformational change in the radical cation during the redox process. The conformational change is rationalized on the basis of the MO calculations. (C) 2004 Elsevier Ltd. All rights reserved.
• Electroactive compounds, compositions and devices and methods of making
  申请人：Elf Atochem North America, Inc.

  公开号：US05334333A1

  公开（公告）日：1994-08-02

  The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices comprised of such electrooptical components, as well as novel processes of making the same.

  本发明涉及一种电活性化合物，该化合物能够在施加电场下发生光吸收和折射变化，并在暴露于预定光辐射波段下发生永久折射变化。本发明还涉及包含这种电活性化合物的电活性组合物，由这种电活性组合物组成的电光组件和由这种电光组件组成的电光设备，以及制造这些物品的新型工艺。