N-diazo-2,4-difluorobenzenesulfonamide | 1152981-02-6

• 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: N-diazo-2,4-difluorobenzenesulfonamide
• CAS: 1152981-02-6
• 化学式: C₆H₃F₂N₃O₂S
• 分子量: 219.172
• InChiKey: XRZWETWVZQZXTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-pivaloyl indole 、 N-diazo-2,4-difluorobenzenesulfonamide 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 silver(I) acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 以83%的产率得到2,4-difluoro-N-(1-pivaloyl-1H-indol-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Iridium(III)-Catalyzed Regioselective C7-Amination of N-Pivaloylindoles with Sulfonoazides

  摘要：

  Direct C7-amination of N-pivaloylindoles has been achieved using a combination of [Cp*IrCl2](2), AgNTf2, and AgOAc as the catalyst and sulfonoazides as the nitrogen source. The reaction proceeded at room temperature to 80 degrees C to afford 7-sulfonamidoindoles in good to excellent yields. The reaction is broadly applicable to the C7-amination of a wide variety of 3-, 4-, 5-, and 6-substituted N-pivaloylindoles with either alkyl or aryl sulfonoazides.

  DOI：

  10.1021/acs.joc.6b01856

文献信息

• Synthesis, biological activities and structure−activity relationships for new avermectin analogues
  作者：Jian Zhang、Xiang Nan、Hai-Tao Yu、Pi-Le Cheng、Yan Zhang、Ying-Qian Liu、Shao-Yong Zhang、Guan-Fang Hu、Huanxiang Liu、An-Liang Chen

  DOI：10.1016/j.ejmech.2016.05.056

  日期：2016.10

  LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 μM, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides.

  为了发现具有良好杀虫活性的新分子，合成了40多种新的阿维菌素衍生物，并评估了它们对三种物种的蜘蛛，昆虫和线虫的生物活性，这些物种分别是朱砂叶螨（Tetranychus Cinnabarinus），蚜虫（Aphis craccivora）和松柏xylophilus。所有测试的化合物均显示出对三种昆虫的有效抑制活性。值得注意的是，大多数化合物对朱砂毛虫表现出高选择性，其中一些与阿维菌素相比具有更好的选择性。特别是化合物9j（LC 50：0.005μM）和16d（LC 50：0.002μM）对朱砂丁香的活性分别比阿维菌素（LC 50： 0.013μM ）高2.5倍和4.7倍。此外，化合物9B，9D-F ，9H，9J，9升，9N，9P，9R，9V和17D显示了优良的活性与LC 50个相比的2.959-5.013μM的值1（LC 50： 6.746μM）对乙。松材线虫。同时，化合物9f，9g，9h和9m的杀虫活性针对A
• Ru-catalyzed direct arene C–H amidation of pyrrolo[2,3-d]pyrimidines with sulfonyl azides
  作者：Yunfeng Jiang、Zhengtong Mao、Yue Guan、Haokun Pan、Xingxian Zhang

  DOI：10.1016/j.tetlet.2021.153569

  日期：2022.1

  Ru-catalyzed direct C–H amidation of pyrrolo[2,3-d]pyrimidine derivatives was developed using sulfonyl azides as the amino source in a mild, efficient and highly chemoselective manner. The promising protocol has good compatibility with diverse functional groups and high regioselectivity, providing various structurally versatile monoamidated pyrrolo[2,3-d]pyrimidines in good to excellent yields with potential

  Ru催化的吡咯并[2,3- d ]嘧啶衍生物的直接C-H酰胺化是使用磺酰叠氮化物作为氨基源以温和、有效和高度化学选择性的方式开发的。有前景的方案与不同的官能团具有良好的兼容性和高区域选择性，提供了各种结构通用的单酰胺化吡咯并[2,3- d ]嘧啶，收率良好，具有潜在的生物和治疗活性。
• Design, Synthesis, Crystal Structure, Insecticidal Activity, Molecular Docking, and QSAR Studies of Novel <i>N</i>₃-Substituted Imidacloprid Derivatives
  作者：Mei-Juan Wang、Xiao-Bo Zhao、Dan Wu、Ying-Qian Liu、Yan Zhang、Xiang Nan、Huanxiang Liu、Hai-Tao Yu、Guan-Fang Hu、Li-Ting Yan

  DOI：10.1021/jf501108j

  日期：2014.6.18

  Three novel series of N3-substituted imidacloprid derivatives were designed and synthesized, and their structures were identified on the basis of satisfactory analytical and spectral ((1)H NMR, (13)C NMR, MS, elemental analysis, and X-ray) data. Preliminary bioassays indicated that all of the derivatives exhibited significant insecticidal activities against Aphis craccivora, with LC50 values ranging from 0.00895 to 0.49947 mmol/L, and the insecticidal activities of some of them were comparable to those of the control imidacloprid. Some key structural features related to their insecticidal activities were identified, and the binding modes between target compounds and nAChR model were also further explored by molecular docking. By comparing the interaction features of imidacloprid and compound 26 with highest insecticidal activity, the origin of the high insecticidal activity of compound 26 was identified. On the basis of the conformations generated by molecular docking, a satisfactory 2D-QSAR model with six selected descriptors was built using genetic algorithm-multiple linear regression (GA-MLR) method. The analysis of the built model showed the molecular size, shape, and the ability to form hydrogen bond were important for insecticidal potency. The information obtained in the study will be very helpful for the design of new derivatives with high insecticidal activities.
• Iridium(III)-Catalyzed Regioselective C7-Amination of <i>N</i>-Pivaloylindoles with Sulfonoazides
  作者：Lanting Xu、Lushi Tan、Dawei Ma

  DOI：10.1021/acs.joc.6b01856

  日期：2016.11.4

  Direct C7-amination of N-pivaloylindoles has been achieved using a combination of [Cp*IrCl2](2), AgNTf2, and AgOAc as the catalyst and sulfonoazides as the nitrogen source. The reaction proceeded at room temperature to 80 degrees C to afford 7-sulfonamidoindoles in good to excellent yields. The reaction is broadly applicable to the C7-amination of a wide variety of 3-, 4-, 5-, and 6-substituted N-pivaloylindoles with either alkyl or aryl sulfonoazides.