ethyl 3-(benzoylamino)-6-(ethoxycarbonyl)methyl-2-oxo-2H-pyran-5-carboxylate

• 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 3-(benzoylamino)-6-(ethoxycarbonyl)methyl-2-oxo-2H-pyran-5-carboxylate
• 英文别名: Ethyl 5-benzamido-2-(2-ethoxy-2-oxoethyl)-6-oxopyran-3-carboxylate
• 化学式: C₁₉H₁₉NO₇
• 分子量: 373.362
• InChiKey: UHUDUFSQLFQHCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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

• A Way to Avoid Using Precious Metals: The Application of High-Surface Activated Carbon for the Synthesis of Isoindoles via the Diels–Alder Reaction of 2<i>H</i>-Pyran-2-ones
  作者：Marko Krivec、Martin Gazvoda、Krištof Kranjc、Slovenko Polanc、Marijan Kočevar

  DOI：10.1021/jo3000783

  日期：2012.3.16

  The application of activated carbon (Darco KB) for the acceleration and direction of the transformation of various 2H-pyran-2-ones with N-substituted maleimides toward isoindole derivatives through the reaction sequence cycloaddition/elimination/dehydrogenation is described. In this reaction, the catalyst mainly influences the dehydrogenation step, which is essential to avoid the formation of bicyclo[2

  活性炭（Darco KB）在加速2和N转化为2 H -pyran-2-one方面的应用描述了通过反应序列环加成/消除/脱氢向异吲哚衍生物取代的马来酰亚胺。在该反应中，催化剂主要影响脱氢步骤，这对于避免形成双环[2.2.2]辛烯以及其他可能的产物至关重要。我们发现，在密闭容器中，Darco KB（无金属催化剂）和十氢化萘（作为溶剂）的组合代表了最成功的条件。还比较了各种脱氢催化剂的效果和反应条件。此外，我们已经证明，芳香化是通过氢从环己二烯中间体转移到马来酰亚胺衍生物（因此产生琥珀酰亚胺）而发生的。非均相碳基催化剂的活性表面促进了这种转移。
• 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。
• An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1016/j.tet.2007.10.099

  日期：2008.1

  The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13-15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxy-ethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5. (c) 2007 Elsevier Ltd. All rights reserved.
• 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
  作者：Amadej Juranovič、Krištof Kranjc、Franc Perdih、Slovenko Polanc、Marijan Kočevar

  DOI：10.1016/j.tet.2011.03.034

  日期：2011.5

  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.