2-[5-(2-oxo-1,2-diphenylethylsulfanyl)-2-thioxo-1,3-dithiol-4-ylsulfanyl]-1,2-diphenyl-1-ethanone | 214494-47-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[5-(2-oxo-1,2-diphenylethylsulfanyl)-2-thioxo-1,3-dithiol-4-ylsulfanyl]-1,2-diphenyl-1-ethanone
• 英文别名: 2-[[5-(2-oxo-1,2-diphenylethyl)sulfanyl-2-sulfanylidene-1,3-dithiol-4-yl]sulfanyl]-1,2-diphenylethanone
• CAS: 214494-47-0
• 化学式: C₃₁H₂₂O₂S₅
• 分子量: 586.844
• InChiKey: CUHWAHMWAQCUGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[5-(2-oxo-1,2-diphenylethylsulfanyl)-2-thioxo-1,3-dithiol-4-ylsulfanyl]-1,2-diphenyl-1-ethanone 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以30%的产率得到5,6-diphenylthieno[2,3-d][1,3]dithiole-2-thione
  参考文献：
  名称：

  5,6-Diphenylthieno[2,3-d][1,3]dithiole-2-thione

  摘要：

  The title compound, C17H10S4, has two independent molecules in the asymmetric unit. In both molecules, the fused heterocycle is almost planar and the phenyl groups make dihedral angles of 42.88 (9) and 52.79 (8)degrees with the fused heterocycle in one molecule, and angles of 40.62 (9) and 52.28 (8)degrees in the other. The crystal packing is governed by short intermolecular S . . .S interactions, the shortest contact being 3.333 (1) Angstrom.

  DOI：

  10.1107/s0108270101010988
• 作为产物：
  描述：

  4,5-dimercapto-1,3-dithiole-2-thione, sodium salt 、 2-氯-2-苯基苯乙酮 以 乙醇 为溶剂， 以90%的产率得到2-[5-(2-oxo-1,2-diphenylethylsulfanyl)-2-thioxo-1,3-dithiol-4-ylsulfanyl]-1,2-diphenyl-1-ethanone
  参考文献：
  名称：

  An important application of the 1,8-diketone ring formation reaction: a concise synthesis of 5,6-diphenyl[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione and its coupling product

  摘要：

  通过1,8-二酮环形成反应，已合成完全不饱和的5,6-二苯基[1,3]二硫醇[4,5-b][1,4]二硫英-2-硫酮及其偶联产物，后者是BEDT-TTF的完全不饱和类似物。

  DOI：

  10.1039/b003714l

文献信息

• An important application of the 1,8-diketone ring formation reaction: a concise synthesis of 5,6-diphenyl[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione and its coupling product
  作者：Erdal Ertas、Turan Ozturk

  DOI：10.1039/b003714l

  日期：——

  Syntheses of fully unsaturated 5,6-diphenyl[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione and its coupling product, a fully unsaturated analogue of BEDT-TTF, have been achieved by a 1,8-diketone ring formation reaction.

  通过1,8-二酮环形成反应，已合成完全不饱和的5,6-二苯基[1,3]二硫醇[4,5-b][1,4]二硫英-2-硫酮及其偶联产物，后者是BEDT-TTF的完全不饱和类似物。
• 5-Benzyl-5-phenyl[1,3]dithiolo[4,5-<i>d</i>][1,3]dithiole-2-thione
  作者：F. Betül Kaynak、Süheyla Özbey、Turan Öztürk、Erdal Ertaş

  DOI：10.1107/s0108270100019764

  日期：2001.3.15

  In the title compound, C17H12S5, the dithiole ring bearing the aryl substituents assumes an envelope conformation with the maximum deviation from planarity being -0.053 Angstrom. The phenyl and benzyl rings are twisted by 33.0 (1) and 31.1 (1)degrees, respectively, out of the dithiole plane. The crystal packing is governed by short S . . .S interactions, with the shortest being 3.550 (2) Angstrom.
• 5,6-Diphenyl[1,3]dithiolo[4,5-<i>b</i>]dithiine-2-thione
  作者：F. Betül Kaynak、Süheyla Özbey、Turan Öztürk、Erdal Ertaş

  DOI：10.1107/s0108270101006679

  日期：2001.8.15

  In the title compound, C17H10S5, the dithiine ring adopts a boat conformation while the dithiole ring has an envelope conformation. The phenyl groups are planar and make dihedral angles of 40.7 (2) and 59.8 (2)degrees with the best plane of the thiine ring. The shortest intermolecular S . . .S contact is 3.305 (2) Angstrom.
• Synthesis of highly functionalized BEDT-TTF analogues incorporating 1,4-dithiin rings from 1,8-diketones
  作者：Erdal Ertas、F. Betul Kaynak、Suheyla Ozbey、Ipek Osken、Turan Ozturk

  DOI：10.1016/j.tet.2008.08.085

  日期：2008.11

  with dihydroxyl, dimethyl, MEM and diphenylthiophene groups. Spectroelectrochemistry of ET and its fully unsaturated analogue 4 was compared. While both displayed nearly similar behaviours, ET started to precipitate as the second oxidation potential is reached. CV studies indicated that the fully unsaturated 4 and tetraphenyldithiophene 20 have the highest oxidation potentials, while diphenyldithiindimethylthio

  使用1，8-二酮环形成反应导致具有二苯基-1，4-二硫辛环以及二羟基，二甲基，MEM和二苯基噻吩基团的四硫富瓦烯衍生物的合成。比较了ET及其完全不饱和类似物4的光谱电化学。尽管两者表现出几乎相似的行为，但随着达到第二氧化电位，ET开始沉淀。CV研究表明，完全不饱和的4和四苯基二噻吩20具有最高的氧化电位，而二苯基二硫代二甲硫基16显示最低的氧化电位。CV测量表明二硫辛和羟基的结合有助于降低氧化电位。令人惊讶的是，尽管二硫辛环的存在导致较高的氧化电势，但是羟基降低了电势。研究了具有二硫辛和1,4-二硫平环的13的单晶结构，观察到二硫辛和二硫平环与平面TTF核呈顺式形成20.52°和25.65°的角，因为两个环都绕着它们弯曲S⋯S轴为船形。
• 5,6-Diphenylthieno[2,3-<i>d</i>][1,3]dithiole-2-thione
  作者：F. Betül Kaynak、Süheyla Özbey、Turan Öztürk、Erdal Ertaş

  DOI：10.1107/s0108270101010988

  日期：2001.9.15

  The title compound, C17H10S4, has two independent molecules in the asymmetric unit. In both molecules, the fused heterocycle is almost planar and the phenyl groups make dihedral angles of 42.88 (9) and 52.79 (8)degrees with the fused heterocycle in one molecule, and angles of 40.62 (9) and 52.28 (8)degrees in the other. The crystal packing is governed by short intermolecular S . . .S interactions, the shortest contact being 3.333 (1) Angstrom.