2,2'-diphenyl-4,4'-bithiazolylidene-5,5'-dione | 1187638-73-8

• 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: 2,2'-diphenyl-4,4'-bithiazolylidene-5,5'-dione
• CAS: 1187638-73-8
• 化学式: C₁₈H₁₀N₂O₂S₂
• 分子量: 350.422
• InChiKey: INNZEKKEVVKMAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.86
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-苯基-4H-1,3-噻唑-5-酮 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以51%的产率得到2,2'-diphenyl-4,4'-bithiazolylidene-5,5'-dione
  参考文献：
  名称：

  The degradation of 4,5-dichloro-1,2,3-dithiazolium chloride in wet solvents

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.086

文献信息

• 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.