1,4-dicyano-2,3-dimethoxycyclopentadiene | 346647-84-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4-dicyano-2,3-dimethoxycyclopentadiene
• 英文别名: 4,5-Dimethoxycyclopenta-3,5-diene-1,3-dicarbonitrile
• CAS: 346647-84-5
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: MXCGQQKLJPHTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dicyano-2,3-dimethoxycyclopentadiene 在 potassium tert-butylate 、 silver nitrate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 5.25h， 以64%的产率得到3,4,3',4'-Tetramethoxy-bicyclopentylidene-2,4,2',4'-tetraene-2,5,2',5'-tetracarbonitrile
  参考文献：
  名称：

  Base-catalyzed condensation of cyclopentadiene derivatives. Synthesis of fulvalene analogues: strong proaromatic electron acceptors

  摘要：

  A series of proaromatic electron acceptors derived from fulvenes were synthesized from tetrachlorocyclopentadiene and previously unknown 1,4-dicyano- and 1,4-dialkoxycarbonyl-2,3-dimethoxy cyclopentadienes. Two reversible one-electron reductions steps observed for fulvalenes coalesce into one two-electron reduction step upon increasing the length of the conjugating bridge. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00877-9
• 作为产物：
  描述：

  重氮甲烷 、 1,4-dicyano-2,3-dihydroxycyclopentadiene 以 乙醚 为溶剂， 反应 0.5h， 以88%的产率得到1,4-dicyano-2,3-dimethoxycyclopentadiene
  参考文献：
  名称：

  Base-catalyzed condensation of cyclopentadiene derivatives. Synthesis of fulvalene analogues: strong proaromatic electron acceptors

  摘要：

  A series of proaromatic electron acceptors derived from fulvenes were synthesized from tetrachlorocyclopentadiene and previously unknown 1,4-dicyano- and 1,4-dialkoxycarbonyl-2,3-dimethoxy cyclopentadienes. Two reversible one-electron reductions steps observed for fulvalenes coalesce into one two-electron reduction step upon increasing the length of the conjugating bridge. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00877-9

文献信息

• Novel D-π-A Chromophores Based on the Fulvene Accepting Moiety
  作者：Emad Aqad、Philippe Leriche、Gilles Mabon、Alain Gorgues、Vladimir Khodorkovsky

  DOI：10.1021/ol016143n

  日期：2001.7.1

  [GRAPHICS]Novel D-pi -A chromophores based on the fulvene accepting moiety and p-dimethylamino phenyl and 1,3-dithiole-2-ylidene donor moieties have been prepared. The X-ray structures of two representative derivatives have been determined. Examination of the UV-visible spectra and cyclic voltamperometry data revealed remarkable sensitivity of the electronic structure of these derivatives to substituents at the cyclopentadiene ring.
• Fulvalene derivatives: strong proaromatic electron acceptors
  作者：Emad Aqad、Philippe Leriche、Gilles Mabon、Alain Gorgues、Vladimir Khodorkovsky

  DOI：10.1016/s0040-4039(01)00327-6

  日期：2001.4

  Synthesis and electrochemical properties of novel proaromatic electron accepters based on the fulvalene parent system are described. (C) 2001 Elsevier Science Ltd. All rights reserved.