2-hydroxy-N-(phenylmethyl)benzenepropanamide | 294652-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-N-(phenylmethyl)benzenepropanamide
• 英文别名: N-benzyl-3-(2-hydroxyphenyl)propanamide
• CAS: 294652-39-4
• 化学式: C₁₆H₁₇NO₂
• mdl: MFCD00433642
• 分子量: 255.316
• InChiKey: ZYDKJXRQMFRRGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氢化肉桂酸内酯 、 苄胺 在 氢化镓 、 碘苯 、 氢化铝 作用下， 以 甲苯 、 touene 为溶剂， 反应 23.17h， 以83%的产率得到2-hydroxy-N-(phenylmethyl)benzenepropanamide
  参考文献：
  名称：

  Direct Reaction of Aryl Iodides with Activated Aluminium Powder and Reactions of the Derived Aryl Sesquiiodides

  摘要：

  高温（110-120°C）下，在HgCl2（1摩尔%）或液态镓金属（10摩尔%）的存在下，ArI（Ar = Ph、1-C10H7、3-Tol）与铝粉直接反应，可定量转化为芳基倍半碘化铝Al2Ar3I3。这些化合物具有极强的路易斯酸性，能有效打开环醚并实现酯到酰胺的直接转化。

  DOI：

  10.1055/s-0029-1219179

文献信息

• Organotin-catalyzed synthesis of hydroxyalkylamides from lactones via a ring-opening process
  作者：Xiayu Liang、Peng Yu、Chen Fu、Yongcun Shen

  DOI：10.1016/j.tetlet.2021.152821

  日期：2021.3

  A new strategy for the facile synthesis of hydroxyalkylamides through the ring-opening reaction of lactone with amine promoted by dibutyltin acetate was developed. A series of hydroxyalkylamide compounds were obtained and the method was successfully applied to the synthesis of pharmaceutically active molecules tyrosinase inhibitor V and HDAC inhibitor VI via a three-step synthetic pathway. The broad

  提出了通过乙酸二丁锡促进内酯与胺的开环反应轻松合成羟烷基酰胺的新策略。获得了一系列羟烷基酰胺化合物，并将该方法成功地通过三步合成途径用于合成药物活性分子酪氨酸酶抑制剂V和HDAC抑制剂VI。广泛的底物范围，温和的反应条件和实际应用证明了该方法的有效性，兼容性和实用性。
• 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.
• Direct Reaction of Aryl Iodides with Activated Aluminium Powder and Reactions of the Derived Aryl Sesquiiodides
  作者：Simon Woodward、Xiaoping Tang、Daniel Rawson

  DOI：10.1055/s-0029-1219179

  日期：2010.3

  High temperature (110-120 ˚C) direct reaction of ArI (Ar = Ph, 1-C10H7, 3-Tol) with aluminium powder in the presence of HgCl2 (1 mol%) or liquid gallium metal (10 mol%) leads to quantitative conversion to the aryl sesquiiodides Al2Ar3I3. The latter, highly Lewis acidic, compounds are effective in opening of cyclic ethers and direct ester to amide conversions.

  高温（110-120°C）下，在HgCl2（1摩尔%）或液态镓金属（10摩尔%）的存在下，ArI（Ar = Ph、1-C10H7、3-Tol）与铝粉直接反应，可定量转化为芳基倍半碘化铝Al2Ar3I3。这些化合物具有极强的路易斯酸性，能有效打开环醚并实现酯到酰胺的直接转化。