4,5-ethylenedioxytetrathiafulvalene | 308797-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶英
• 英文名称: 4,5-ethylenedioxytetrathiafulvalene
• 英文别名: Methyl 2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxin-2-ylidene)-1,3-dithiole-4-carboxylate
• CAS: 308797-09-3
• 化学式: C₁₀H₈O₄S₄
• 分子量: 320.435
• InChiKey: PZASQDVXCDXFMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-ethylenedioxytetrathiafulvalene 在 lithium bromide 作用下， 以 六甲基磷酰三胺 为溶剂， 以50%的产率得到4,5-ethylenedioxy-tetrathiafulvalene
  参考文献：
  名称：

  Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes

  摘要：

  4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)(3)-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.

  DOI：

  10.3987/com-00-s(i)79
• 作为产物：
  描述：

  4,5-bis(methoxycarbonyl)-1,3-dithiole-2-one 在 lithium bromide 、 亚磷酸三乙酯 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 5.75h， 生成 4,5-ethylenedioxytetrathiafulvalene
  参考文献：
  名称：

  Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes

  摘要：

  4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)(3)-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.

  DOI：

  10.3987/com-00-s(i)79

文献信息

• Papavassiliou, G. C.; Kakoussis, V. C.; Lagouvardos, D. J., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 181, p. 171 - 184
  作者：Papavassiliou, G. C.、Kakoussis, V. C.、Lagouvardos, D. J.、Mousdis, G. A.

  DOI：——

  日期：——
• Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes
  作者：Masahiko Iyoda、Yoshiyuki Kuwatani、Eiji Ogura、Kenji Hara、Hironori Suzuki、Takahiro Takano、Koji Takeda、Jun-ichi Takano、Kohei Ugawa、Masato Yoshida、Haruo Matsuyama、Hiroyuki Nishikawa、Isao Ikemoto、Takehiro Kato、Naoki Yoneyama、Jun-ichi Nishijo、Akira Miyazaki、Toshiaki Enoki

  DOI：10.3987/com-00-s(i)79

  日期：——

  4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)(3)-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.