N-{4-[(Z)-2-(4-nitrophenyl)vinyl]phenyl}acetamide | 1426055-78-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-{4-[(Z)-2-(4-nitrophenyl)vinyl]phenyl}acetamide
• 英文别名: (E)-N-[4-(4-nitrostyryl)phenyl]acetamide；N-[4-[(Z)-2-(4-nitrophenyl)ethenyl]phenyl]acetamide
• CAS: 1426055-78-8
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: KMYUHKCVKYYXKJ-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4′-氨基乙酰苯胺 在 tetrafluoroboric acid 、 亚硝酸特丁酯 、 palladium diacetate 作用下， 以 甲醇 、 水 为溶剂， 反应 17.2h， 生成 N-{4-[(Z)-2-(4-nitrophenyl)vinyl]phenyl}acetamide 、 N-{4-[(E)-2-(4-nitrophenyl)vinyl]phenyl}acetamide
  参考文献：
  名称：

  乙酰氨基芳烃重氮盐：多芳烃功能化的机会

  摘要：

  与它们的邻位对应物不同，间和对乙酰氨基苯胺可以转化为相应的乙酰氨基芳烃重氮盐。这些为多种 Pd 催化的芳烃官能化反应提供了各种机会，例如 Matsuda-Heck-、Suzuki-Miyaura- 或 Fujiwara-Moritani 偶联。

  DOI：

  10.1002/ejoc.201500795

文献信息

• Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema
  作者：Takayuki Inoue、Masataka Morita、Takashi Tojo、Kousei Yoshihara、Akira Nagashima、Ayako Moritomo、Mitsuru Ohkubo、Hiroshi Miyake

  DOI：10.1016/j.bmc.2012.12.025

  日期：2013.3

  Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema.In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats. (C) 2013 Elsevier Ltd. All rights reserved.
• Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionali­zation
  作者：Bernd Schmidt、Nelli Elizarov、Nastja Riemer、Frank Hölter

  DOI：10.1002/ejoc.201500795

  日期：2015.9

  Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.

  与它们的邻位对应物不同，间和对乙酰氨基苯胺可以转化为相应的乙酰氨基芳烃重氮盐。这些为多种 Pd 催化的芳烃官能化反应提供了各种机会，例如 Matsuda-Heck-、Suzuki-Miyaura- 或 Fujiwara-Moritani 偶联。