4-fluoro-5-trifluoromethyl-3H-1,2-dithiole-3-thione | 485403-05-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-fluoro-5-trifluoromethyl-3H-1,2-dithiole-3-thione
• 英文别名: 4-fluoro-5-trifluoromethyl-1,2-dithiole-3-thione；4-Fluoro-5-(trifluoromethyl)dithiole-3-thione
• CAS: 485403-05-2
• 化学式: C₄F₄S₃
• 分子量: 220.236
• InChiKey: LGMIWXNOGROMCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-fluoro-5-trifluoromethyl-3H-1,2-dithiole-3-thione 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 3-imino and 3-ylideno derivatives of 4-fluoro-5-polyfluoroalkyl-1,2-dithiolenes

  摘要：

  Reactions of 4-fluoro-5-polyfluoroalkyl-1,2-dithiol-3-thiones with hydroxylamine and hydrazines occur with replacement of the thiocarbonyl by imino group affording oximes and hydrazones respectively. N-Alkyl- and N-aryl-3-imino-1,2-dithiolenes formed in reactions of 3-chlorothio-1,2-dithiolium salts with primary alkyl- or arylamines. 3-Chlorothio-1,2-dithiolium salts react with compounds possessing an active methylene group yielding 3-ylideno derivatives of 1,2-dithiolenes.

  DOI：

  10.1134/s1070428002120187
• 作为产物：
  描述：

  1,1-bis(ethylsulfanyl)perfluorobut-1-ene 在 sulfur 、 magnesium bromide 作用下， 反应 0.08h， 以92%的产率得到4-fluoro-5-trifluoromethyl-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  氟化乙烯酮二硫缩醛。第九部分 新型氟化3 H -1,2-二硫代-3-硫酮的合成及一些化学性质

  摘要：

  通过将相应的乙烯酮二硫缩醛与溴化镁和元素硫一起加热，制得4-氟-5-全氟烷基-3 H -1,2-二硫基-3-硫酮。它们在环加成反应中以亲双烯体和1,3-偶极子的形式反应，生成新的氟化有机硫化合物。

  DOI：

  10.1016/s0040-4039(02)01179-6

文献信息

• Successive Cycloadditions between 4-Fluoro-5-trifluoromethyl-1,2-dithiole-3-thione and Dimethyl Acetylenedicarboxylate: New Fluorinated Thiaheterocycles through New Reaction Mechanisms
  作者：Vadim M. Timoshenko、Jean-Philippe Bouillon、Alexander N. Chernega、Yuriy G. Shermolovich、Charles Portella

  DOI：10.1002/ejoc.200300036

  日期：2003.7

  The cycloaddition reaction between dimethyl 2-(1-fluoro-2-trifluoromethyl-2-thioxoethylidene)-1,3-dithiole-4,5-dicarboxylate and dimethyl acetylenedicarboxylate proceeds efficiently under irradiation conditions in air. A study of the reaction conditions resulted in the proposal of a chain mechanism initiated by a photochemically induced single-electron transfer to oxygen. On the other hand, the cycloadduct

  2-(1-氟-2-三氟甲基-2-硫代亚乙基)-1,3-二硫醇-4,5-二甲酸二甲酯和乙炔二甲酸二甲酯之间的环加成反应在空气中的辐照条件下有效进行。对反应条件的研究提出了由光化学诱导的单电子转移到氧引发的链式机制。另一方面，环加合物可以通过硅胶过滤转化为重排的羟基化产物。环加合物或其重排产物可以在一锅法中从母体 1,2-二硫醇-3-硫酮中选择性地获得。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of 3-imino and 3-ylideno derivatives of 4-fluoro-5-polyfluoroalkyl-1,2-dithiolenes
  作者：I. N. Fesun、V. M. Timoshenko、Yu. G. Shermolovich

  DOI：10.1134/s1070428002120187

  日期：2006.2

  Reactions of 4-fluoro-5-polyfluoroalkyl-1,2-dithiol-3-thiones with hydroxylamine and hydrazines occur with replacement of the thiocarbonyl by imino group affording oximes and hydrazones respectively. N-Alkyl- and N-aryl-3-imino-1,2-dithiolenes formed in reactions of 3-chlorothio-1,2-dithiolium salts with primary alkyl- or arylamines. 3-Chlorothio-1,2-dithiolium salts react with compounds possessing an active methylene group yielding 3-ylideno derivatives of 1,2-dithiolenes.
• Fluorinated ketene dithioacetals. Part IX. Synthesis and some chemical properties of new fluorinated 3H-1,2-dithiole-3-thiones
  作者：Vadim M Timoshenko、Jean-Philippe Bouillon、Yuriy G Shermolovich、Charles Portella

  DOI：10.1016/s0040-4039(02)01179-6

  日期：2002.8

  4-Fluoro-5-perfluoroalkyl-3H-1,2-dithiole-3-thiones were prepared by heating the corresponding ketene dithioacetals with magnesium bromide and elemental sulfur. They reacted as dienophiles and 1,3-dipoles in cycloaddition reactions to give new fluorinated organosulfur compounds.

  通过将相应的乙烯酮二硫缩醛与溴化镁和元素硫一起加热，制得4-氟-5-全氟烷基-3 H -1,2-二硫基-3-硫酮。它们在环加成反应中以亲双烯体和1,3-偶极子的形式反应，生成新的氟化有机硫化合物。