[5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazol-2-yl](triphenylphosphoranylidene)acetonitrile | 1120356-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazol-2-yl](triphenylphosphoranylidene)acetonitrile
• 英文别名: 2-[4-tosyl-5-(p-chlorophenylsulfonyl)-1,3-thiazol-2-yl]triphenylphosphoranylideneacetonitrile；2-[5-(4-chlorophenyl)sulfonyl-4-(4-methylphenyl)sulfonyl-1,3-thiazol-2-yl]-2-(triphenyl-λ5-phosphanylidene)acetonitrile
• CAS: 1120356-74-2
• 化学式: C₃₆H₂₆ClN₂O₄PS₃
• 分子量: 713.238
• InChiKey: FAHPGLDXJLGIRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazol-2-yl](triphenylphosphoranylidene)acetonitrile 、 sodium thiophenolate 以 四氢呋喃 为溶剂， 反应 24.0h， 以77%的产率得到2-(5-((4-chlorophenyl)sulfonyl)-4-(phenylthio)thiazol-2-yl)-2-(triphenyl-l5-phosphaneylidene)acetonitrile
  参考文献：
  名称：

  Biphilic properties of substituted triphenylphosphoranylideneacetonitriles bearing 4,5-Di(arylsulfonyl)-1,3-thiazol-2-yl fragments at the ylide center

  摘要：

  Phosphonium ylides stabilized by nitrile and 4,5-di(arylsulfonyl)-1,3-thiazol-2-yl fragments show biphilic reactivity. They react with aromatic aldehydes upon heating revealing a noticeable activity of ylide center and are condensed with typical nucleophiles at C(4) center of the thiazole ring with the elimination of arylsulfanyl group tinder mild conditions. New 1,3-thiazole derivatives were obtained whose structures were proved by chemical, special and X-ray structural investigations.

  DOI：

  10.1134/s107036320907010x
• 作为产物：
  描述：

  2-(benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazole 、 (三苯基膦)乙腈 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以74%的产率得到[5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazol-2-yl](triphenylphosphoranylidene)acetonitrile
  参考文献：
  名称：

  Biphilic properties of substituted triphenylphosphoranylideneacetonitriles bearing 4,5-Di(arylsulfonyl)-1,3-thiazol-2-yl fragments at the ylide center

  摘要：

  Phosphonium ylides stabilized by nitrile and 4,5-di(arylsulfonyl)-1,3-thiazol-2-yl fragments show biphilic reactivity. They react with aromatic aldehydes upon heating revealing a noticeable activity of ylide center and are condensed with typical nucleophiles at C(4) center of the thiazole ring with the elimination of arylsulfanyl group tinder mild conditions. New 1,3-thiazole derivatives were obtained whose structures were proved by chemical, special and X-ray structural investigations.

  DOI：

  10.1134/s107036320907010x

文献信息

• Reaction of 2-(Benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazole with O-, N-, S-, and C-nucleophiles
  作者：K. V. Turov、B. S. Drach

  DOI：10.1134/s1070363208040208

  日期：2008.4

  2-(Benzenesulfonyl)-4-tosyl-1,3-thiazole was synthesized starting from the available 2,2-dichloro-1-tosylethenyl isothiocyanate. The product is a pronounced electrophilic substrate feasible for investigation of the order of nucleophilic substitution at the C(2), C(4), and C(5) centers of the thiazole ring. Different nucleophilic agent first attack the C(2) atom. After that S-nucleophiles react with C(5), while O- and N-nucleophiles, with C(4).