2-amino-N-(3-phenylpropyl)benzamide | 49667-91-6

• 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: 2-amino-N-(3-phenylpropyl)benzamide
• CAS: 49667-91-6
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: MHNBSAFWMNXVBU-UHFFFAOYSA-N

物化性质

• 沸点：
  476.5±38.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-N-(3-phenylpropyl)benzamide 在 palladium diacetate 、 C₂₃H₂₈NO₂P 、 caesium carbonate 、 二异丙胺 、 三氯氧磷 、 三甲基乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (S)-methyl 3-methyl-2-(4-oxo-3-(3-phenylpropyl)-3,4-dihydroquinazolin-2-yl)benzoate
  参考文献：
  名称：

  钯催化的2-异氰基苯甲酰胺的对映体选择性偶联环化，以构建轴向手性的2-芳基和2,3-二芳基喹唑啉酮

  摘要：

  已经开发了具有2,6-二取代的芳基碘化物的钯催化的N-烷基-2-异氰基苯甲酰胺的酰亚胺化环酰胺化，其提供了空前的轴向手性2-芳基喹唑啉酮，具有良好的收率和对位选择性。在该偶联-环化过程中，联芳基键和杂芳环一步一步形成。当将N-（2，4-二甲氧基苯基）-2-异氰基苯甲酰胺用作底物时，产生具有两个立体异构轴的2，3-二芳基喹唑啉酮具有适度的非对映选择性和良好的对映选择性。

  DOI：

  10.1021/jacs.1c00640
• 作为产物：
  描述：

  3-苯基-1-丙胺 、 邻氨基苯甲酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-amino-N-(3-phenylpropyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel small molecule inhibitors of the influenza virus protein NS1

  摘要：

  Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The existing vaccination program is variably effective from year to year, and drug resistance to available antivirals is a growing problem, making the development of additional antivirals an important challenge. Influenza virus non-structural protein 1 (NS1) is the centerpiece of the viral response to the host interferon (IFN) system. NS1 was demonstrated previously to be a potential therapeutic target for antiviral therapy by the identification of specific small-molecule inhibitors. One inhibitory compound, NSC125044, was subjected to chemical evaluation. Initial synthetic work comprised simplifying the core structure by removing unwanted functionality and determination of key features important for activity. Several subclasses of molecules were designed and synthesized to further probe activity and develop the basis for a structure-activity relationship. Apparent potency, as judged by activity in virus replication assays, increased dramatically for some analogs, without cytotoxicity. Results suggest that the target binding site tolerates hydrophobic bulk as well as having a preference for weakly basic substituents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.026

文献信息

• FeCl₃-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical
  作者：Yingying Yang、Xianglin Yu、Na He、Xinxiang Huang、Xizhong Song、Jingbo Chen、Jun Lin、Yi Jin

  DOI：10.1039/d3cc03186a

  日期：——

  broad substrate scope (60 examples) and offer operationally simple, scalable procedures for accessing valuable products from methylarenes in a single step. Mechanistic studies and control experiments confirm the participation of a photogenerated chlorine radical in facilitating the hydrogen atom transfer (HAT) from the benzylic C–H bond to initiate the reaction.

  在此，我们报告了通过光诱导配体到金属电荷转移（LMCT）的铁催化苄基C-H氧化酰胺化反应的进展。这些反应展示了广泛的底物范围（60 个示例），并提供了操作简单、可扩展的程序，可通过一步从甲基芳烃中获取有价值的产物。机理研究和控制实验证实光生氯自由基参与促进氢原子从苄基C-H键转移（HAT）以引发反应。
• 2-ACYLAMINOBENZAMIDE DERIVATIVES AND PREVENTIVE AND REMEDY FOR DISEASES CAUSED BY THE SUPERMULTIPLICATION OF VASCULAR INTIMAL CELLS
  申请人：KISSEI PHARMACEUTICAL CO., LTD.

  公开号：EP0855387A1

  公开（公告）日：1998-07-29

  The present invention relates to 2-acylaminobenzamide derivatives represented by the general formula: wherein R1, R2, R3, R4 and R5 represent each a hydrogen atom etc.; X represents a vinylene group etc.; B represents a group represented by the general formula:         -N(R6)(R7) wherein R6 and R7 represent each a hydrogen atom etc., a group represented by the general formula:         -NH-(CH2)n-A-R8 wherein A represents a single bond etc.; R8 represents a hydroxy group etc. or a hydroxyamino group which are useful as agents for the prevention and treatment of diseases caused by excessive proliferation of vascular intimal cells.

  本发明涉及由通式表示的 2-酰氨基苯甲酰胺衍生物： 其中R1、R2、R3、R4和R5分别代表氢原子等；X代表乙烯基等；B代表通式所代表的基团： -N(R6)(R7) 其中 R6 和 R7 各自代表一个氢原子等；B 代表由通式表示的基团： -NH-(CH2)n-A-R8 其中 A 代表单键等；R8 代表羟基等或羟基氨基，它们可用作预防和治疗因血管内膜细胞过度增殖而引起的疾病的药物。
• Gravier; Dupin; Casadebaig, Pharmazie, 1992, vol. 47, # 2, p. 91 - 94
  作者：Gravier、Dupin、Casadebaig、Hou、Boisseau、Bernard

  DOI：——

  日期：——
• EP855387
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis, and evaluation of novel small molecule inhibitors of the influenza virus protein NS1
  作者：Joseph J. Jablonski、Dipwanita Basu、Daniel A. Engel、H. Mario Geysen

  DOI：10.1016/j.bmc.2011.10.026

  日期：2012.1

  Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The existing vaccination program is variably effective from year to year, and drug resistance to available antivirals is a growing problem, making the development of additional antivirals an important challenge. Influenza virus non-structural protein 1 (NS1) is the centerpiece of the viral response to the host interferon (IFN) system. NS1 was demonstrated previously to be a potential therapeutic target for antiviral therapy by the identification of specific small-molecule inhibitors. One inhibitory compound, NSC125044, was subjected to chemical evaluation. Initial synthetic work comprised simplifying the core structure by removing unwanted functionality and determination of key features important for activity. Several subclasses of molecules were designed and synthesized to further probe activity and develop the basis for a structure-activity relationship. Apparent potency, as judged by activity in virus replication assays, increased dramatically for some analogs, without cytotoxicity. Results suggest that the target binding site tolerates hydrophobic bulk as well as having a preference for weakly basic substituents. (C) 2011 Elsevier Ltd. All rights reserved.