1-苯甲酰基-5-硝基吲唑 | 23856-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯甲酰基-5-硝基吲唑
• 英文名称: 1-benzoyl-5-nitroindazole
• 英文别名: (5-nitro-1H-indazol-1-yl)(phenyl)methanone；1-Benzoyl-5-nitro-1H-indazol；1-benzoyl-5-nitro-1H-indazole；(5-nitroindazol-1-yl)-phenylmethanone
• CAS: 23856-15-7
• 化学式: C₁₄H₉N₃O₃
• 分子量: 267.244
• InChiKey: YOHMDFWMHMUDDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯甲酰基-5-硝基吲唑 在 乙醇 、 锌 作用下， 生成 1-苯甲酰基-1H-吲唑-5-胺
  参考文献：
  名称：

  吲唑衍生物：各种氨基吲哚和羟基吲唑及其衍生磺酸的合成

  摘要：

  DOI：

  10.1039/jr9550002412
• 作为产物：
  描述：

  benzoic acid-(2-chloro-5-nitro-benzylidenehydrazide) 在 铜 、 potassium carbonate 、 potassium iodide 作用下， 生成 1-苯甲酰基-5-硝基吲唑
  参考文献：
  名称：

  Meisenheimer; Senn, Chemische Berichte, 1926, vol. 59, p. 201

  摘要：

  DOI：

文献信息

• Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
  作者：D. M. M. Mevan Dissanayake、Aaron K. Vannucci

  DOI：10.1021/acs.orglett.8b03683

  日期：2019.1.18

  An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This “anion pool” approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles

  已经开发了用于吲唑的选择性N 1酰化的电化学合成方法。这种“阴离子池”方法通过电化学方式还原吲唑分子，从而生成吲唑阴离子和H 2。然后将酸酐引入溶液中，导致吲唑的N1位选择性酰化。该方法也可用于苯并咪唑和吲哚的酰化。也可以使用9 V电池进行反应，而不会损失反应效率。
• Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis
  作者：Sateesh Kumar Arepalli、Chaerim Lee、Jae-Kyung Jung、Youngsoo Kim、Kiho Lee、Heesoon Lee

  DOI：10.1016/j.bmcl.2019.07.055

  日期：2019.9

  We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of alpha-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified 3k and 6g as lead compounds which displayed almost 5 and 9 times more potent inhibition of alpha-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R-3) for the compounds (3a-p) and presence of +M group at ortho position (R-5) for the compounds (6a-j) were crucial for their excellent inhibition activities of alpha-MSH-stimulated melanogenesis.
• Uff, Barrie C.; Ho, Yee-Ping; Brown, David S., Journal of Chemical Research, Miniprint, 1989, # 11, p. 2652 - 2681
  作者：Uff, Barrie C.、Ho, Yee-Ping、Brown, David S.、Fisher, Ian、Popp, Frank D.、Kant, Joydeep

  DOI：——

  日期：——
• v. Auwers; Schwegler, Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227
  作者：v. Auwers、Schwegler

  DOI：——

  日期：——