(E)-allyl 3-(butylamino)-2-(1,4-dioxo-1,4-dihydronaphth-2-yl)but-2-enoate | 1439385-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-allyl 3-(butylamino)-2-(1,4-dioxo-1,4-dihydronaphth-2-yl)but-2-enoate
• 英文别名: prop-2-enyl (E)-3-(butylamino)-2-(1,4-dioxonaphthalen-2-yl)but-2-enoate
• CAS: 1439385-93-9
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: APHRGHNXKNOGDO-XMHGGMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-allyl 3-(butylamino)-2-(1,4-dioxo-1,4-dihydronaphth-2-yl)but-2-enoate 在 ammonium cerium (IV) nitrate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以55%的产率得到allyl 1-butyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate
  参考文献：
  名称：

  A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors

  摘要：

  The CAN-catalyzed three-component reaction between primary amines, beta-ketoesters and naphthoquinone in ethanol at room temperature afforded as the main products the corresponding Michael adducts, oxidized to the quinone stage. When these compounds were refluxed in ethanol in the presence of CAN, they afforded tricyclic ortho-quinones derived from the benzo[g]indole-4,5-dione framework via a domino mechanism comprising a sequence of 5-exo-trig cyclization, elimination, Michael addition, oxo-enol tautomerism and hydroquinone oxidation individual steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.101
• 作为产物：
  描述：

  乙酰乙酸烯丙酯 、 正丁胺 、 1,4-萘醌 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 、 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到(E)-allyl 3-(butylamino)-2-(1,4-dioxo-1,4-dihydronaphth-2-yl)but-2-enoate
  参考文献：
  名称：

  A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors

  摘要：

  The CAN-catalyzed three-component reaction between primary amines, beta-ketoesters and naphthoquinone in ethanol at room temperature afforded as the main products the corresponding Michael adducts, oxidized to the quinone stage. When these compounds were refluxed in ethanol in the presence of CAN, they afforded tricyclic ortho-quinones derived from the benzo[g]indole-4,5-dione framework via a domino mechanism comprising a sequence of 5-exo-trig cyclization, elimination, Michael addition, oxo-enol tautomerism and hydroquinone oxidation individual steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.101

文献信息

• A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors
  作者：Padmakar A. Suryavanshi、Vellaisamy Sridharan、J. Carlos Menéndez

  DOI：10.1016/j.tet.2013.04.101

  日期：2013.7

  The CAN-catalyzed three-component reaction between primary amines, beta-ketoesters and naphthoquinone in ethanol at room temperature afforded as the main products the corresponding Michael adducts, oxidized to the quinone stage. When these compounds were refluxed in ethanol in the presence of CAN, they afforded tricyclic ortho-quinones derived from the benzo[g]indole-4,5-dione framework via a domino mechanism comprising a sequence of 5-exo-trig cyclization, elimination, Michael addition, oxo-enol tautomerism and hydroquinone oxidation individual steps. (C) 2013 Elsevier Ltd. All rights reserved.