2-((4-methoxyphenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide | 134697-02-2

• 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: 2-((4-methoxyphenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-[(4-Methoxyphenoxy)methyl]-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 134697-02-2
• 化学式: C₁₅H₁₃NO₅S
• 分子量: 319.338
• InChiKey: GXPLDRWFSAIZDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-methoxyphenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide 在 buffer 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 聚合甲醛 、 4-甲氧基苯酚 、 糖精
  参考文献：
  名称：

  Mechanism of hydrolysis of O-imidomethyl derivatives of phenols

  摘要：

  Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied. Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives. Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions. The more acidic the imide or the phenol, the faster the rate of hydrolysis. However, the rates of hydrolysis were more sensitive to the acidity of the phenol. Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an S(N)2 reaction. An amide derivative was found to hydrolyze more slowly than predicted from the analogous imide series and the pK(a) of the amide. This result is apparently due partially to stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C (=O)N group and hence more accessible to nucleophilic attack.

  DOI：

  10.1021/jo00070a029
• 作为产物：
  描述：

  N-羟基甲基糖精 在 五氯化磷 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 2-((4-methoxyphenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
  参考文献：
  名称：

  Mechanism of hydrolysis of O-imidomethyl derivatives of phenols

  摘要：

  Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied. Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives. Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions. The more acidic the imide or the phenol, the faster the rate of hydrolysis. However, the rates of hydrolysis were more sensitive to the acidity of the phenol. Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an S(N)2 reaction. An amide derivative was found to hydrolyze more slowly than predicted from the analogous imide series and the pK(a) of the amide. This result is apparently due partially to stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C (=O)N group and hence more accessible to nucleophilic attack.

  DOI：

  10.1021/jo00070a029

文献信息

• Efficient imidation of C(sp³)–H bonds adjacent to oxygen atoms of aryl ethers under metal-free conditions
  作者：Kai Sun、Xin Wang、Gang Li、Zhonghong Zhu、Yongqing Jiang、Beibei Xiao

  DOI：10.1039/c4cc06003b

  日期：——

  An intermolecular oxidative C-N formation reaction of aryl ethers with pharmacological saccharins was realized under metal-free conditions for the first time. The understanding of the intrinsic characteristics between C(sp(3))-H and C(sp(2))-O bonds of aryl ethers and their potential for application might promote more research interest in this area.

  首次在无金属条件下实现了芳基醚与药理糖精的分子间氧化CN形成反应。对芳基醚的C（sp（3））-H和C（sp（2））-O键之间的固有特征的理解及其应用潜力可能会促进该领域的研究兴趣。