2-dicyanomethylthieno[3,2-b]thiophene | 183309-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2-dicyanomethylthieno[3,2-b]thiophene
• 英文别名: 2-Thieno[3,2-b]thiophen-5-ylpropanedinitrile
• CAS: 183309-04-8
• 化学式: C₉H₄N₂S₂
• 分子量: 204.276
• InChiKey: IVTDDNHJWRAHRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylthio-1,3-dithiolium methyl sulfate 、 2-dicyanomethylthieno[3,2-b]thiophene 在 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以83%的产率得到2-(dicyanomethylene)-5-(1,3-dithiol-2-ylidene)-2,5-dihydrothieno[3,2-b]thiophene
  参考文献：
  名称：

  Syntheses, Structures, and Spectroscopic Properties of Push-Pull Heteroquinoid Compounds

  摘要：

  DOI：

  10.3987/com-06-10848
• 作为产物：
  描述：

  噻吩并[3,2-b]噻吩 在 bis-triphenylphosphine-palladium(II) chloride 碘 、 叔丁基锂 、 sodium hydride 作用下， 反应 26.33h， 生成 2-dicyanomethylthieno[3,2-b]thiophene
  参考文献：
  名称：

  Efficient Synthesis of 2-Iodo and 2-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno[3,2-b]thiophene

  摘要：

  An effective synthesis of 2-iodothiophene, 2-iodotellurophene, and 2-iodothieno[3,2-b]thiophene and a Pd-catalyzed carbon-carbon coupling reaction of these iodo derivatives as well as 2-iodoselenophene with malononitrile affording novel thienyl-, tellurienyl-, thieno[3,2-b]thienyl-, and selenienylmalononitrile are described. These heteroarylmalononitriles are important synthons for the preparation of 2-dicyanomethylene-2,5-dihydroheterophene chromophores.

  DOI：

  10.3987/com-96-7517

文献信息

• Push–pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene moiety: synthesis, ground state polarization and second-order nonlinear properties
  作者：A. Belén Marco、Raquel Andreu、Santiago Franco、Javier Garín、Jesús Orduna、Belén Villacampa、Beatriz E. Diosdado、Juan T. López Navarrete、Juan Casado

  DOI：10.1039/c3ob41278d

  日期：——

  first time the reactivity of this system towards aldehydes. Their ground state polarization and linear and second-order nonlinear optical (NLO) properties have been determined by a combined experimental and theoretical study, and compared to those of analogous compounds featuring an aromatic thienothiophene unit. Due to the gaining of aromaticity, quinoid systems have been found to display more polarized

  已经合成了以醌型形式 带有2-二氰基亚甲基噻吩并[3,2- b ]噻吩部分的发色团，这是首次探索该体系对醛的反应性。通过结合实验和理论研究，确定了它们的基态极化以及线性和二阶非线性光学（NLO）特性，并将其与具有芳香族噻吩并噻吩单元的类似化合物进行了比较。由于获得了芳香性，已发现醌类系统相对于其芳香族对应物显示出更多的极化电子基态和更高的NLO响应。
• (Super)gelators derived from push–pull chromophores: synthesis, gelling properties and second harmonic generation
  作者：A. Belén Marco、Denis Gindre、Konstantinos Iliopoulos、Santiago Franco、Raquel Andreu、David Canevet、Marc Sallé

  DOI：10.1039/c8ob00251g

  日期：——

  New organogelators including push–pull chromophores are described and show that second harmonic generation active materials can be prepared without sophisticated processes.

  描述了包括推-拉色团在内的新有机凝胶剂，并表明可以制备出不需要复杂过程的二次谐波产生材料。
• Syntheses, Structures, and Spectroscopic Properties of Push-Pull Heteroquinoid Compounds
  作者：Tetsuo Otsubo、Shinobu Inoue、Shinji Mikami、Kazuo Takimiya、Yoshio Aso

  DOI：10.3987/com-06-10848

  日期：——
• Efficient Synthesis of 2-Iodo and 2-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno[3,2-b]thiophene
  作者：Kazuko Takahashi、Shinji Tarutani

  DOI：10.3987/com-96-7517

  日期：——

  An effective synthesis of 2-iodothiophene, 2-iodotellurophene, and 2-iodothieno[3,2-b]thiophene and a Pd-catalyzed carbon-carbon coupling reaction of these iodo derivatives as well as 2-iodoselenophene with malononitrile affording novel thienyl-, tellurienyl-, thieno[3,2-b]thienyl-, and selenienylmalononitrile are described. These heteroarylmalononitriles are important synthons for the preparation of 2-dicyanomethylene-2,5-dihydroheterophene chromophores.