4,5-ethylenedioxy-4',5'-bis(methoxycarbonyl)tetrathiafulvalene | 130156-09-1

• 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-ethylenedioxy-4',5'-bis(methoxycarbonyl)tetrathiafulvalene
• 英文别名: BMCEDO-TTF；Dimethyl 2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxin-2-ylidene)-1,3-dithiole-4,5-dicarboxylate
• CAS: 130156-09-1
• 化学式: C₁₂H₁₀O₆S₄
• 分子量: 378.472
• InChiKey: XGBCLFDVOMETIC-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±45.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-ethylenedioxy-4',5'-bis(methoxycarbonyl)tetrathiafulvalene 在 lithium bromide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 1.75h， 生成 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：

  5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine-2-selone 在 mercury(II) diacetate 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 0.33h， 生成 4,5-ethylenedioxy-4',5'-bis(methoxycarbonyl)tetrathiafulvalene
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Unsymmetrically Substituted Ethylenedioxytetrathiafulvalenes
  作者：Takehiko Mori、Hiroo Inokuchi、Aravinda M. Kini、Jack M. Williams

  DOI：10.1246/cl.1990.1279

  日期：1990.8

  Seven new electron donors, 4,5-ethylenedioxytetrathiafulvalenes where 4′,5′-substituents are trimethylenedithio, ethylenedithio, methylenedithio, 2-oxatrimethylenedithio, methylthio, hydrogen and methyl carboxylate, are prepared, and their electrochemical properties are investigated.

  制备了七种新的电子供体--4,5-亚乙二氧基四硫杂戊烯，其中 4′,5′-取代基为三亚甲基二硫、亚乙基二硫、亚甲基二硫、2-氧杂三亚甲基二硫、甲硫基、氢和羧酸甲酯。
• An organic superconductor, (TEA)(HEDO-TTF-dc)₂·2(H₂C₂O₄), coupled with strong hydrogen-bonding interactions
  作者：Yuto Morimachi、Mizuki Urai、Ryota Nakajima、Hajime Kamebuchi、Kazuya Miyagawa、Kazushi Kanoda、Biao Zhou

  DOI：10.1039/d3cc00080j

  日期：——

  organic superconductor (TEA)(HEDO-TTF-dc)2·2(H2C2O4) (H2EDO-TTF-dc = ethylenedioxy-tetrathiafulvalene dicarboxylic acids) with an onset TC of 4.0 K, was successfully obtained using oxalic acid and HEDO-TTF-dc anion donor. The crystal structure analysis indicated that strong π–π overlaps and very strong intra- and inter-molecular hydrogen-bonding interactions exist between the HEDO-TTF-dc anion donors

  一种新的有机超导体 (TEA)(HEDO-TTF-dc) 2 ·2(H 2 C 2 O 4 ) (H 2 EDO-TTF-dc = 亚乙基二氧基-四硫富瓦烯二羧酸)，起始T C为 4.0 K，是使用草酸和 HEDO-TTF-dc 阴离子供体成功获得。晶体结构分析表明，HEDO-TTF-dc 阴离子供体和草酸分子之间存在强烈的 π-π 重叠和非常强的分子内和分子间氢键相互作用。
• 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.