2-((4-chlorophenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide | 150423-20-4

• 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-chlorophenoxy)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-[(4-Chlorophenoxy)methyl]-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 150423-20-4
• 化学式: C₁₄H₁₀ClNO₄S
• 分子量: 323.757
• InChiKey: KGHAYJFCWYMHCN-UHFFFAOYSA-N

物化性质

• 沸点：
  524.4±56.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-chlorophenoxy)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 、 对氯苯酚 、 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-chlorophenoxy)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。
• FATTY ACID AMIDE HYDROLASE INHIBITORS
  申请人：Makriyannis Alexandros

  公开号：US20090306016A1

  公开（公告）日：2009-12-10

  Disclosed are compounds of formula R—X—Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CB1i and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.

  公开了一种R-X-Y式化合物，可用于抑制脂肪酸酰胺水解酶（FAAH）的作用。抑制脂肪酸酰胺水解酶（FAAH）将减缓FAAH水解作用引起的内源性大麻素配体的正常降解和失活，并允许更高水平的内源性大麻素配体保持存在。这些更高水平的内源性大麻素配体提供了对大麻素CB1i和CB2受体的增加刺激，并产生与大麻素受体激活相关的生理效应。它们还将增强其他外源性大麻素配体的效果，并允许它们在较低浓度下产生其效果，与不抑制脂肪酸酰胺水解酶（FAAH）作用的系统相比。因此，一种抑制脂肪酸酰胺水解酶（FAAH）对内源性大麻素配体失活的化合物可能会增加内源性大麻素的水平，从而增强大麻素受体的激活。因此，该化合物可能不直接调节大麻素受体，但通过增加内源性大麻素配体的水平间接刺激大麻素受体。它还可以增强其他外源性大麻素配体的效果和作用持续时间，这些配体被用于引发大麻素反应。
• Methods and Compounds for Modulating Cannabinoid Activity
  申请人：Makriyannis Alexandros

  公开号：US20110071178A1

  公开（公告）日：2011-03-24

  Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.

  本文披露了一些抑制单酰基甘油脂肪酶（MGL）和脂肪酸酰胺水解酶（FAAH）作用的化合物和组合物，抑制MGL和FAAH的方法，调节大麻素受体的方法，以及治疗与大麻素受体调节相关的各种疾病的方法。
• MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY
  申请人：Makriyannis Alexandros

  公开号：US20110039874A1

  公开（公告）日：2011-02-17

  Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.

  公开了一种抑制单酰基甘油酯脂肪酶（MGL）和脂肪酸酰胺水解酶（FAAH）作用的化合物和组合物，抑制MGL和FAAH的方法，调节大麻素受体的方法，以及治疗与大麻素受体调节相关的各种疾病的方法。
• US9102622B2
  申请人：——

  公开号：US9102622B2

  公开（公告）日：2015-08-11