2,5-bis(hydroxydiphenylmethyl)thieno[3,2-b]thiophene | 145448-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(hydroxydiphenylmethyl)thieno[3,2-b]thiophene
• 英文别名: [5-[Hydroxy(diphenyl)methyl]thieno[3,2-b]thiophen-2-yl]-diphenylmethanol
• CAS: 145448-97-1
• 化学式: C₃₂H₂₄O₂S₂
• 分子量: 504.673
• InChiKey: GWZJMEDNEAROCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis(hydroxydiphenylmethyl)thieno[3,2-b]thiophene 在 trimethylsilyl perchlorate 、 锌 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 2,5-Dibenzhydrylidenethieno[3,2-b]thiophene
  参考文献：
  名称：

  Preparation, Structure, and Redox Behavior of Bis(diarylmethylene)dihydrothiophene and Its π-Extended Analogues

  摘要：

  The preparation, X-ray structure, and optoelectronic properties of bis(diarylmethylene)dihydrothiophene 1 and its p-extended analogues 2 are described. The development of a simple, short-step synthetic route allowed us to prepare derivatives with different aryl units. X-ray crystallographic analysis of 1b and 2b revealed their quinoidal structures, which exhibit strong electronic absorption in the visible region. Cyclic voltammetry measurements revealed their strong electron-donating properties. 1b showed two-step electrochromic behavior between the corresponding radical cation and dication.

  DOI：

  10.1021/acs.joc.5b00021
• 作为产物：
  描述：

  噻吩并[3,2-b]噻吩 、 二苯甲酮 生成 2,5-bis(hydroxydiphenylmethyl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  噻吩取代的三苯甲基型醇的固态溶剂分解：气固接触诱导的亲核取代。

  摘要：

  已经研究了通过气固接触的亲核取代反应。当将9-噻吩并噻吩芴-9-ol衍生物与二氯二氰基醌（DDQ）共研磨，然后暴露于甲醇蒸气中时，以15-70％的产率获得相应的9-甲氧基芴。在整个过程中，固态保持不变。ESR光谱表明，通过底物醇与DDQ之间的电荷转移相互作用，在共研磨的固体中生成了自由基阳离子。基于溶液中底物的电化学氧化，推导了涉及自由基阳离子分解产生质子的机理，该质子充当提供碳正离子的催化剂。对于与甲醇蒸气接触的碳正离子，已经显示出固态的取代反应的传播。将以甲醇为客体的9-噻吩并噻吩基芴-9-醇衍生物的结晶包合物暴露于HCl气体中。该气固反应还导致形成保持固态的相应甲氧基化合物。通过这项工作，得出了固态共研磨的新结果。

  DOI：

  10.1021/jo001291x

文献信息

• Solid-state solvolysis induced via charge-transfer complexation by solid-phase grinding followed by contact with solvent vapor
  作者：Motoko Tanaka、Keiji Kobayashi

  DOI：10.1039/a803496f

  日期：——

  When 9-thienothienylfluoren-9-ol derivatives were ground together with DDQ then exposed to methanol vapor, solvolysis occurred to yield 9-methoxyfluorenes via the generation of a radical cation by solid-state single-electron transfer.

  当9-噻吩噻吩基荧光醇衍生物与DDQ共同研磨后暴露于甲醇蒸气中时，发生了亲核溶解反应，通过固态单电子转移生成自由基阳离子，从而生成9-甲氧基荧光素。
• Tanaka, Motoko; Kobayashi, Keiji, Phosphorus, Sulfur and Silicon and the Related Elements, 1999, vol. 153, p. 371 - 372
  作者：Tanaka, Motoko、Kobayashi, Keiji

  DOI：——

  日期：——
• Solid-State Solvolysis of Thiophene-Substituted Trityl-Type Alcohols:  Nucleophilic Substitution Induced by Gas−Solid Contact
  作者：Motoko Tanaka、Naoki Tanifuji、Shigeru Hatada、Keiji Kobayashi

  DOI：10.1021/jo001291x

  日期：2001.2.1

  suggested by the ESR spectrum. The mechanism involving the collapse of the radical cation to generate a proton, which acts as a catalyst to afford the carbocation, was deduced based on the electrochemical oxidation of the substrate in solution. The propagation of the substitution reaction in the solid state has been shown for the carbocation upon contact with methanol vapor. The crystalline inclusion

  已经研究了通过气固接触的亲核取代反应。当将9-噻吩并噻吩芴-9-ol衍生物与二氯二氰基醌（DDQ）共研磨，然后暴露于甲醇蒸气中时，以15-70％的产率获得相应的9-甲氧基芴。在整个过程中，固态保持不变。ESR光谱表明，通过底物醇与DDQ之间的电荷转移相互作用，在共研磨的固体中生成了自由基阳离子。基于溶液中底物的电化学氧化，推导了涉及自由基阳离子分解产生质子的机理，该质子充当提供碳正离子的催化剂。对于与甲醇蒸气接触的碳正离子，已经显示出固态的取代反应的传播。将以甲醇为客体的9-噻吩并噻吩基芴-9-醇衍生物的结晶包合物暴露于HCl气体中。该气固反应还导致形成保持固态的相应甲氧基化合物。通过这项工作，得出了固态共研磨的新结果。
• Preparation, Structure, and Redox Behavior of Bis(diarylmethylene)dihydrothiophene and Its π-Extended Analogues
  作者：Takashi Takeda、Tomoyuki Akutagawa

  DOI：10.1021/acs.joc.5b00021

  日期：2015.2.20

  The preparation, X-ray structure, and optoelectronic properties of bis(diarylmethylene)dihydrothiophene 1 and its p-extended analogues 2 are described. The development of a simple, short-step synthetic route allowed us to prepare derivatives with different aryl units. X-ray crystallographic analysis of 1b and 2b revealed their quinoidal structures, which exhibit strong electronic absorption in the visible region. Cyclic voltammetry measurements revealed their strong electron-donating properties. 1b showed two-step electrochromic behavior between the corresponding radical cation and dication.