(Z)-4-(benzylamino)-3-phenylbut-3-en-2-one | 1415129-27-9

• 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: (Z)-4-(benzylamino)-3-phenylbut-3-en-2-one
• CAS: 1415129-27-9
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: LNDRPJPEJIIQOA-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基叠氮 、 苄叉丙酮 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以13%的产率得到(Z)-4-(benzylamino)-3-phenylbut-3-en-2-one
  参考文献：
  名称：

  Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide

  摘要：

  Reaction of benzalacetones and dibenzalacetones with benzyl azide promoted by BF3 center dot OEt2 afforded Z and E densely substituted acyclic alpha-aryl enaminones in 21-95% yield. For benzalacetones major Z-isomers were obtained, while E-isomers were the tendency for dibenzalacetones. The synthesis involves domino 1,3-dipolar cycloaddition and 1,2-aryl migration, and is the first metal free practical alternative to the preparation of acyclic alpha-aryl enaminones from commercial available or easily prepared starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.125

文献信息

• An Efficient and Highly Diastereoselective Synthesis of GSK1265744, a Potent HIV Integrase Inhibitor
  作者：Huan Wang、Matthew D. Kowalski、Ami S. Lakdawala、Frederick G. Vogt、Lianming Wu

  DOI：10.1021/ol503580t

  日期：2015.2.6

  A novel synthesis of GSK1265744, a potent HIV integrase inhibitor, is described. The synthesis is highlighted by an efficient construction of the densely functionalized pyridinone core as well as a highly diastereoselective formation of the acyl oxazolidine moiety. The latter exploits the target molecule’s ability to chelate to Mg2+, a key feature in the integrase inhibitor’s mechanism of action.

  描述了一种有效的HIV整合酶抑制剂GSK1265744的新型合成方法。高效官能的吡啶酮酮核的有效构建以及酰基恶唑烷部分的高度非对映选择性形成突出了该合成过程。后者利用靶分子螯合Mg 2+的能力，Mg 2+是整合酶抑制剂作用机制的关键特征。
• Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide
  作者：Silvio Cunha、Amenson Trindade Gomes

  DOI：10.1016/j.tetlet.2012.09.125

  日期：2012.12

  Reaction of benzalacetones and dibenzalacetones with benzyl azide promoted by BF3 center dot OEt2 afforded Z and E densely substituted acyclic alpha-aryl enaminones in 21-95% yield. For benzalacetones major Z-isomers were obtained, while E-isomers were the tendency for dibenzalacetones. The synthesis involves domino 1,3-dipolar cycloaddition and 1,2-aryl migration, and is the first metal free practical alternative to the preparation of acyclic alpha-aryl enaminones from commercial available or easily prepared starting materials. (C) 2012 Elsevier Ltd. All rights reserved.