2-((4-nitrophenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide | 109538-88-7

• 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-nitrophenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-[(4-Nitrophenoxy)methyl]-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione；2-[(4-nitrophenoxy)methyl]-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 109538-88-7
• 化学式: C₁₄H₁₀N₂O₆S
• 分子量: 334.309
• InChiKey: VFIPPRKNMLBVJY-UHFFFAOYSA-N

物化性质

• 沸点：
  592.3±56.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((4-nitrophenoxy)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 、 对硝基苯酚 、 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-nitrophenoxy)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。
• Saccharin derivatives useful as proteolytic enzyme inhibitors and
  申请人：Sanofi

  公开号：US05650422A1

  公开（公告）日：1997-07-22

  Novel 2-substituted saccharins which inhibit the enzymatic activity of proteolytic enzymes, are useful in the treatment of degenerative diseases and have the formula ##STR1## wherein: L is --O--, --S--, --SO-- or --SO.sub.2 --; m and n are each independently 0 or 1; R.sub.1 is halo, lower-alkanoyl, 1-oxophenalenyl, phenyl or substituted phenyl, heterocyclyl or substitued heterocyclyl or, when L is --O-- and n is 1, cycloheptatrienon-2-yl or, when L is --S-- and n is 1, cyano or lower-alkoxythiocarbonyl or, when L is --SO.sub.2 -- and n is 1, lower-alkyl or trifluoromethyl; R.sub.2 is hydrogen, lower-alkoxycarbonyl, phenyl or phenylthio; and R.sub.3 and R.sub.4 are each hydrogen or various substituents and processes for preparation and pharmaceutical compositions and method of use thereof are disclosed.

  这是一种化合物，可用于治疗退行性疾病，具有抑制蛋白酶酶活性的作用。其化学式为：##STR1## 其中：L为--O--、--S--、--SO--或--SO.sub.2 --；m和n各自独立地为0或1；R.sub.1为卤素、低烷酰基、1-氧代苯并茂、苯基或取代苯基、杂环基或取代杂环基，或当L为--O--且n为1时，为环庚三烯-2-基，或当L为--S--且n为1时，为氰基或低烷氧硫酰基，或当L为--SO.sub.2 --且n为1时，为低烷基或三氟甲基；R.sub.2为氢、低烷氧羰基、苯基或苯基硫；R.sub.3和R.sub.4各自为氢或不同的取代基。该化合物的制备方法、药物组合物及使用方法也被揭示。
• 2-Substituted saccharin derivative proteolytic enzyme inhibitors
  申请人：STERLING WINTHROP INC.

  公开号：EP0542372A1

  公开（公告）日：1993-05-19

  Novel 2-substituted saccharins which inhibit the enzymatic activity of proteolytic enzymes are useful in the treatment of degenerative diseases and have the formula    wherein:    L is -O-, -S-, -SO- or -SO₂-;    m and n are each independently 0 or 1;    R₁ is substituted phenyl, heterocyclyl or substitued heterocyclyl or,    when L is -O- and n is 1, R₁ is cycloheptatrienon-2-yl or,    when L is -S- and n is 1, R₁ is cyano or lower-alkoxythiocarbonyl or,    when L is -SO₂- and n is 1, R₁ is lower-alkyl or trifluoromethyl;    R₂ is hydrogen, lower-alkoxycarbonyl, phenyl or phenylthio; and    R₃ and R₄ are each hydrogen or various substituents,    and processes for preparation and pharmaceutical compositions and method of use thereof are disclosed.

  新型 2-取代糖精能抑制蛋白水解酶的酶活性，可用于治疗退行性疾病，其分子式为 其中 L是-O-、-S-、-SO-或-SO₂-； m 和 n 各自独立地为 0 或 1； R₁ 是取代的苯基、杂环基或取代的杂环基；或 当 L 为-O-且 n 为 1 时，R₁ 为环庚三壬-2-基，或 当 L 为-S-且 n 为 1 时，R₁ 为氰基或低级烷氧基硫代羰基；或 当 L 为-SO₂- 且 n 为 1 时，R₁ 为低级烷基或三氟甲基； R₂ 是氢、低级烷氧基羰基、苯基或苯硫基；以及 R₃ 和 R₄ 各为氢或各种取代基、 本发明公开了制备工艺、药物组合物及其使用方法。
• 2-Saccharinylmethyl aryl carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0594257A1

  公开（公告）日：1994-04-27

  Novel 4-R⁴-R⁵-2-Saccharinylmethyl aryl carboxylates of formula I prepared by reacting a 4-R⁴-R⁵-2-halomethylsaccharin with an arylcarboxylic acid in the presence of an acid-acceptor, compositions thereof and their use in the treatment of degenerative diseases are described.

  式 I 的新型 4-R⁴-R⁵-2-糖精甲基芳基羧酸盐 描述了在酸受体存在的情况下，通过使 4-R⁴-R⁵-2-卤甲基糖精与芳基羧酸反应而制备的式 I 的新型 4-R⁴-R⁵-2-糖精甲基芳基羧酸盐、其组合物及其在治疗退行性疾病中的用途。
• SACCHARIN DERIVATIVES USEFUL AS PROTEOLYTIC ENZYME INHIBITORS AND PREPARATION THEREOF
  申请人：STERLING WINTHROP INC.

  公开号：EP0471756A1

  公开（公告）日：1992-02-26