Methyl 3-acetamido-4-chlorobenzoate

• 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: Methyl 3-acetamido-4-chlorobenzoate
• 英文别名: Methyl 3-(acetylamino)-4-chlorobenzoate
• 化学式: C₁₀H₁₀ClNO₃
• mdl: MFCD04352422
• 分子量: 227.647
• InChiKey: HBUXTEJUSPXOQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-acetamido-4-chlorobenzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies

  摘要：

  Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1H-1,2,3-triazole, CN, COOMe, CONHNH2, CONHMe, NO2, NH2, NHCOMe and NHCSNH2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC50 values are lower than those of their corresponding prototypes. Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.05.013
• 作为产物：
  描述：

  3-氨基-4-氯苯甲酸甲酯 、 乙酸酐 以 二氯甲烷 为溶剂， 生成 Methyl 3-acetamido-4-chlorobenzoate
  参考文献：
  名称：

  Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies

  摘要：

  Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1H-1,2,3-triazole, CN, COOMe, CONHNH2, CONHMe, NO2, NH2, NHCOMe and NHCSNH2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC50 values are lower than those of their corresponding prototypes. Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.05.013

文献信息

• Highly<i>ortho</i>-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
  作者：Xiaodong Xiong、Ying-Yeung Yeung

  DOI：10.1002/anie.201607388

  日期：2016.12.23

  An organocatalytic, highly facile, efficient, and regioselective ortho‐chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied

  描述了苯胺的有机催化，高度简便，有效和区域选择性邻氯化反应。已经使用仲氯化铵盐作为催化剂，并且该反应可以在室温下进行而无需保护空气和湿气。另外，该反应易于扩展，并且催化剂可以再循环和再利用。该催化方案已用于高效合成高效c-Met激酶抑制剂。机理研究表明，仲氯化铵盐的独特结构特征对于亲电子邻氯化反应的催化和区域选择性均很重要。
• Direct Electrochemical Ritter‐Type Amination of Electron‐Deficient Arenes
  作者：Youtian Fu、Ling Zhang、Maolin Sun、Liming Cao、Lei Yang、Ruihua Cheng、Yueyue Ma、Jinxing Ye

  DOI：10.1002/ejoc.202300553

  日期：2023.9.14

  method is characterized by inexpensive and easily accessible regents, atom and step economy. With moderate to good yields, this useful and simple process produces a number of acetanilides from simple electron-deficient arenes, including mono-, di-, and tri-substituted arenes.

  开发了一种在温和条件下用于缺电子 C(sp 2 )−H Ritter 型胺化的实用且直接方法的电化学方案。该方法的特点是试剂便宜且易于获得、原子和步骤经济。这种有用且简单的方法可以从简单的缺电子芳烃（包括单取代、二取代和三取代芳烃）产生多种乙酰苯胺，产率中等至良好。