3H,6H-1,2-dithiolo<4,3-c>1,2-dithiole-3-one-6-thione | 87747-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 3H,6H-1,2-dithiolo<4,3-c>1,2-dithiole-3-one-6-thione
• 英文别名: 6-thioxo-3,6-dihydro[1,2]dithiolo[4,3-c][1,2]dithiol-3-one；1,2-Dithiolo[4,3-c][1,2]dithiole-3-one-6-thione；3H,6H-1,2-dithiolo[4,3-c]1,2-dithiole-3-one-6-thione；6h-1,2-Dithiolo[4,3-c]1,2-dithiole-3-one-6-thione；6-sulfanylidenedithiolo[4,3-c]dithiol-3-one
• CAS: 87747-20-4
• 化学式: C₄OS₅
• 分子量: 224.373
• InChiKey: UUIHXXVEERTLHX-UHFFFAOYSA-N

物化性质

• 熔点：
  221 °C
• 沸点：
  388.6±52.0 °C(Predicted)
• 密度：
  2.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3H,6H-1,2-dithiolo<4,3-c>1,2-dithiole-3-one-6-thione 以90%的产率得到
  参考文献：
  名称：

  KORDTS, BERND;RICHTER, ANDREAS M.;FANGHANEL, EGON, MONATSH. CHEM., 122,(1991) N-2, C. 71-75

  摘要：

  DOI：
• 作为产物：
  描述：

  3H,6H-<1,2>dithiolo<4,3-c><1,2>dithiole-3,6-dithione 在 硫酸 作用下， 以28.9%的产率得到3H,6H-1,2-dithiolo<4,3-c>1,2-dithiole-3-one-6-thione
  参考文献：
  名称：

  Addition compounds of nucleophiles and 3-ethylthio-6-oxo-6H-1,2-dithiolo[4,3-c]1,2-dithiolium tetrafluoroborate. Synthesis of 3H,6H-1,2-dithiolo[4,3-c]1,2-dithiole-3-one-6-thione

  摘要：

  A smooth method of synthesizing 3H, 6H-1,2-dithiolo[4,3-c]1,2-dithiole-3,6-dithione (3), and also its partial desulfuration to yield 3H, 6H-1,2-dithiolo[4,3-c]1,2-dithiole-3-one-6-thione (4) is presented. The ethylation product 5 of the monothione 4 reacts with various nucleophilic reagents to form remarkably stable adducts. The adducts of 5 with methanol, tert-butyl mercaptan, and with aniline could be isolated and characterized by their H-1-NMR spectra.

  DOI：

  10.1007/bf00815167

文献信息

• Cycloaddition Reactions of [1,2]Dithiolo[1,2]dithiole Derivatives with Dimethyl Acetylenedicarboxylate: Formation of New Bi-, Tri- and Tetracyclic Thiopyran Derivatives
  作者：E. Fanghänel、T. Palmer、J. Kersten、R. Ludwigs、K. Peters、H. G. Von Schnering

  DOI：10.1055/s-1994-25639

  日期：——

  By cycloaddition reactions of the title compounds 1, new spiro[1,3-dithiole-thiopyran] derivatives 3 and 5 are available. Their cleavage with mercury(II) acetate leads to the corresponding bicyclic thiopyran-4-ones 9 and 10. Starting from 3H,6H-[1,2]dithiolo[4,3-c][1,2]dithiole- 3,6-dithione (1d), besides 4H,8H-2,3,6,7,4′,5′,4″,5″- octa-(methoxycarbonyl)thiopyrano[3,2-b]thiopyran-4-spiro-2′-(1′,3′- dithiole)-8-spiro-2″-(1″,3″-dithiole) (5), the tetra(5′,6′- methoxycarbonyl-1′,4′-dithiino)[2,3-c][2,3-e][2,3-i] [2,3-k]-1,2,7,8-tetrathiacyclododeca-3,5,9,11-tetraene (8) is formed.

  通过标题化合物 1 的环加成反应，可以得到新的螺[1,3-二硫代-噻喃]衍生物 3 和 5。它们与乙酸汞（II）发生裂解反应，得到相应的双环噻喃-4-酮 9 和 10。从 3H,6H-[1,2]二硫环戊并[4,3-c][1,2]二硫杂环戊烯-3,6-二硫酮（1d）开始，除了 4H,8H-2,3,6,7,4′,5′,4″,5″-八-（甲氧羰基）噻喃并[3,2-b]噻喃-4-螺-2′-（1′、4-螺-2′-(1′, 3′-二硫代)-8-螺-2″-(1″, 3″-二硫代)(5)，形成四(5′, 6′-甲氧羰基-1′, 4′-二硫代)[2,3-c][2,3-e][2,3-i][2,3-k]-1,2,7,8-四硫基环十二碳-3,5,9,11-四烯(8)。
• Fanghaenel, E.; Richter, A. M.; Kordts, B., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 43, # 1-2, p. 165 - 186
  作者：Fanghaenel, E.、Richter, A. M.、Kordts, B.、Beye, N.

  DOI：——

  日期：——
• Donatorsubstituierte Polyacetylene und Analoga II. Notiz über die Synthese einfacher Derivate des neuen heterobicyclischen Grundkörpers 3H,6H-1,2-dithiolo[4,3-c](1,2)-dithiol
  作者：Andreas M. Richter、Egon Fanghänel

  DOI：10.1016/s0040-4039(00)88172-1

  日期：1983.1
• KORDTS, BERND;RICHTER, ANDREAS M.;FANGHANEL, EGON, MONATSH. CHEM., 122,(1991) N-2, C. 71-75
  作者：KORDTS, BERND、RICHTER, ANDREAS M.、FANGHANEL, EGON

  DOI：——

  日期：——
• Addition compounds of nucleophiles and 3-ethylthio-6-oxo-6H-1,2-dithiolo[4,3-c]1,2-dithiolium tetrafluoroborate. Synthesis of 3H,6H-1,2-dithiolo[4,3-c]1,2-dithiole-3-one-6-thione
  作者：Bernd Kordts、Andreas M. Richter、Egon Fangh�nel

  DOI：10.1007/bf00815167

  日期：——

  A smooth method of synthesizing 3H, 6H-1,2-dithiolo[4,3-c]1,2-dithiole-3,6-dithione (3), and also its partial desulfuration to yield 3H, 6H-1,2-dithiolo[4,3-c]1,2-dithiole-3-one-6-thione (4) is presented. The ethylation product 5 of the monothione 4 reacts with various nucleophilic reagents to form remarkably stable adducts. The adducts of 5 with methanol, tert-butyl mercaptan, and with aniline could be isolated and characterized by their H-1-NMR spectra.