(4E)-4-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dihydro-5-oxothiazole-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4E)-4-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dihydro-5-oxothiazole-2-carbonitrile
• 英文别名: 4-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-cyano-4H-thiazol-5-one；(4E)-4-(4-chlorodithiazol-5-ylidene)-5-oxo-1,3-thiazole-2-carbonitrile
• 化学式: C₆ClN₃OS₃
• 分子量: 261.737
• InChiKey: ISJOBCBZIXLKSY-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  142
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,5-二氯-1,2,3-二噻唑氯化物 在 水 、 二甲基亚砜 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以69%的产率得到4-氯二噻唑-5-酮
  参考文献：
  名称：

  The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with DMSO: an improved synthesis of 4-chloro-1,2,3-dithiazol-5H-one

  摘要：

  4,5-Dichloro-1,2,3-dithiazolium chloride 2 (Appel salt) reacts with either DMSO, diphenylsulfoxide 11 or methylphenylsulfoxide 12 to give 4-chloro-5H-1,2,3-dithiazol-5-one 1 in excellent yields. The use of catalytic amounts of DMSO (1 mol%) in MeCN in the presence of water (1 equiv) transforms Appel salt 2 into dithiazolone 1 in near quantitative yields (92%). Rational mechanisms are proposed to explain the catalytic nature of these reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.075

文献信息

• Conversion of tetrazoles into hydrazonoyl chlorides. Novel donor–dithiazolium interactions
  作者：Charles W. Rees、Sivaprasad Sivadasan、Andrew J. P. White、David J. Williams

  DOI：10.1039/b202211g

  日期：2002.6.27

  5-Substituted tetrazoles 13, readily prepared from RCN and aluminium azide, react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides 16 in high yield. 5-Aminotetrazole 4 reacts further to give the extended bis(iminodithiazole) 6 and a minor product 7. Mechanisms are proposed for these reactions (except for the formation of 7) which are supported by the smooth conversion of

  5位替补 四唑 13，由RCN和叠氮化铝在室温下，与Appel盐1迅速反应，以高收率得到酰氯16。5-氨基四唑4进一步反应，得到延伸的双（亚氨基二噻唑）6和次要产物7。提出了这些反应的机理（除了7的形成以外），这些机理由5-氨基-2-取代基的平滑转化得到支持。四唑 11，但不被5-氨基-1-取代四唑，分为正常的亚氨基二噻唑类。12。红色的双（亚胺）6在温暖的条件下重排为黄色的1,3,4-噻二唑19二甲基亚砜。的结构1，6，7和19被证明X射线晶体学 这也表明在每种情况下，相邻的二噻唑环硫原子与任一氧之间都存在很强的3中心分子间相互作用， 氮 或氯供体。
• The degradation of 4,5-dichloro-1,2,3-dithiazolium chloride in wet solvents
  作者：Andreas S. Kalogirou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.086

  日期：2009.8

  4,5-Dichloro-1,2,3-dithiazolium chloride 1 (Appel salt) reacts in wet DCM, THF or MeCN to give elemental sulfur, dithiazole-5-thione 4, dithiazol-5-one 5 and thiazol-5-one 6. Furthermore the reaction of 2-phenylthiazol-5(4H)-one 12 with Appel salt 1 at ca. 20 degrees C gives 4-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-phenylthiazol-5(4H)-one 13 (26%) while at ca. 82 degrees C a new product 2,2'-diphenyl-4,4'-bithiazol-ylidene-5,5'-dione 14 (36%) is additionally isolated. Finally, 4,4'-bithiazolylidene-5,5'-dione 14 is prepared directly by treating 2-phenylthiazol-5(4H)-one 12 with N-chlorosuccinimide. All new Compounds are fully characterised and rational mechanisms are proposed for the formation of all key compounds. (C) 2009 Elsevier Ltd. All rights reserved.
• The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with DMSO: an improved synthesis of 4-chloro-1,2,3-dithiazol-5H-one
  作者：Andreas S. Kalogirou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.075

  日期：2009.8

  4,5-Dichloro-1,2,3-dithiazolium chloride 2 (Appel salt) reacts with either DMSO, diphenylsulfoxide 11 or methylphenylsulfoxide 12 to give 4-chloro-5H-1,2,3-dithiazol-5-one 1 in excellent yields. The use of catalytic amounts of DMSO (1 mol%) in MeCN in the presence of water (1 equiv) transforms Appel salt 2 into dithiazolone 1 in near quantitative yields (92%). Rational mechanisms are proposed to explain the catalytic nature of these reactions. (C) 2009 Elsevier Ltd. All rights reserved.