3-(1-Methyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile | 736178-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(1-Methyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile
• 英文别名: 3-(1-methyl-2,2-dioxo-3H-2,1-benzothiazol-3-yl)propanenitrile
• CAS: 736178-06-6
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: FRYBYMMNUWRJHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1-Methyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile 以 邻二氯苯 为溶剂， 反应 0.5h， 以68%的产率得到(E)-4-(2-Methylamino-phenyl)-but-3-enenitrile
  参考文献：
  名称：

  A new approach for the ortho -substitution of anilines and for the synthesis of indolines

  摘要：

  Intermolecular radical addition of a xanthate to a vinyl sulfanilide is followed by ring closure to the aromatic ring to give a dihydrobenzoisothiazole dioxide structure, which upon heating loses sulfur dioxide to give a 2-substituted aniline; in some examples, the presence of DBU during heating induces the formation of an indoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.111
• 作为产物：
  描述：

  S-cyanomethyl O-ethyl carbonodithioate 、 N-methyl-N-phenylethenesulfonamide 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 以70%的产率得到3-(1-Methyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile
  参考文献：
  名称：

  A new approach for the ortho -substitution of anilines and for the synthesis of indolines

  摘要：

  Intermolecular radical addition of a xanthate to a vinyl sulfanilide is followed by ring closure to the aromatic ring to give a dihydrobenzoisothiazole dioxide structure, which upon heating loses sulfur dioxide to give a 2-substituted aniline; in some examples, the presence of DBU during heating induces the formation of an indoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.111

文献信息

• A new approach for the ortho -substitution of anilines and for the synthesis of indolines
  作者：Cécile Moutrille、Samir Z. Zard

  DOI：10.1016/j.tetlet.2004.04.111

  日期：2004.6

  Intermolecular radical addition of a xanthate to a vinyl sulfanilide is followed by ring closure to the aromatic ring to give a dihydrobenzoisothiazole dioxide structure, which upon heating loses sulfur dioxide to give a 2-substituted aniline; in some examples, the presence of DBU during heating induces the formation of an indoline. (C) 2004 Elsevier Ltd. All rights reserved.