bis(1,4-dihydroxynaphtho)tetrathiafulvalene | 65160-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(1,4-dihydroxynaphtho)tetrathiafulvalene
• 英文别名: 2-(4,9-Dihydroxybenzo[f][1,3]benzodithiol-2-ylidene)benzo[f][1,3]benzodithiole-4,9-diol
• CAS: 65160-06-7
• 化学式: C₂₂H₁₂O₄S₄
• 分子量: 468.599
• InChiKey: HSROHJRCVGZODE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  182
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis(1,4-dihydroxynaphtho)tetrathiafulvalene 在 sodium hypochlorite 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以87%的产率得到(2,3)-(6,7)-bis(1,4-naphthoquinone)tetrathiafulvalene
  参考文献：
  名称：

  Tetrathiafulvalene quinones, hydroquinones and esters

  摘要：

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.

  DOI：

  10.1016/s0040-4020(01)89885-9
• 作为产物：
  描述：

  benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-one 在 sodium dithionite 、 亚磷酸三乙酯 作用下， 以 乙醇 、 苯 为溶剂， 生成 bis(1,4-dihydroxynaphtho)tetrathiafulvalene
  参考文献：
  名称：

  Tetrathiafulvalene quinones, hydroquinones and esters

  摘要：

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.

  DOI：

  10.1016/s0040-4020(01)89885-9

文献信息

• DEMETRIADIS N. G.; HUANG S. J.; SAMULSKI E. T., TETRAHEDRON LETT. <TELE-AY>, 1977, NO 26, 2223-2226
  作者：DEMETRIADIS N. G.、 HUANG S. J.、 SAMULSKI E. T.

  DOI：——

  日期：——
• Tetrathiafulvalene quinones, hydroquinones and esters
  作者：William H Watson、Etim E Eduok、Ram P Kashyap、Mariusz Krawiec

  DOI：10.1016/s0040-4020(01)89885-9

  日期：1993.4

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.