ethyl 5-(benzoylamino)-2-[(ethoxycarbonyl)methyl]benzoate | 1093676-49-3

• 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: ethyl 5-(benzoylamino)-2-[(ethoxycarbonyl)methyl]benzoate
• CAS: 1093676-49-3
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: GHUMGFQXLSRXLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 ethyl 3-(benzoylamino)-6-(ethoxycarbonyl)methyl-2-oxo-2H-pyran-5-carboxylate 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以73%的产率得到ethyl 5-(benzoylamino)-2-[(ethoxycarbonyl)methyl]benzoate
  参考文献：
  名称：

  Comparison of the reaction pathways and intermediate products of a microwave-assisted and high-pressure-promoted cycloaddition of vinyl-moiety-containing dienophiles on 2H-pyran-2-ones

  摘要：

  A comparative study of the reaction pathway of the cycloaddition of various vinyl-containing dienophiles on a set of substituted 3-acylamino-2H-pyran-2-ones under microwave-assisted and high-pressure conditions is presented. In the course of the reaction both the intermediate products, i.e., the 2-oxabicyclo[2.2.2]oct-5-ene (the exo/endo selectivity depended upon the dienophile) and the alkoxycyclohexadiene systems, were isolated and comprehensively characterized; this included X-ray diffraction analyses. The role of the base (DABCO) as an organocatalyst was further elucidated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.034

文献信息

• Ethyl Vinyl Ether as a Synthetic Equivalent of Acetylene in a DABCO-Catalyzed Microwave-Assisted Diels-Alder-Elimination Reaction Sequence Starting from 2<i>H</i>-Pyran-2-ones
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1055/s-0028-1083515

  日期：——

  We present a study of the Diels-Alder reaction between various electron-deficient 2H-pyran-2-ones and ethyl vinyl ether. This microwave-accelerated sequence of a cycloaddition followed by a retro-Diels-Alder reaction (the elimination of CO 2 ) and a second elimination step ofEtOH yields substituted aniline derivatives. The reaction sequence is greatly accelerated by the application of DABCO as a suitable

  我们研究了各种缺电子 2H-pyran-2-ones 与乙基乙烯基醚之间的 Diels-Alder 反应。这种微波加速的环加成顺序，随后是逆狄尔斯-阿尔德反应（CO 2 的消除）和EtOH的第二个消除步骤，产生取代的苯胺衍生物。使用 DABCO 作为合适的碱大大加快了反应顺序。