N-[(1RS,4SR,8RS)-6-acetyl-8-ethoxy-1-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-4-yl]benzamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(1RS,4SR,8RS)-6-acetyl-8-ethoxy-1-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-4-yl]benzamide
• 英文别名: N-[rel-(1S,4R,8S)-6-Acetyl-8-ethoxy-1-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-4-yl]benzamide；N-[(1S,4R,8S)-6-acetyl-8-ethoxy-1-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-4-yl]benzamide
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: NBAPRBKDOSMMPS-ZYSHUDEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)-benzamide 、 乙烯基乙醚 在 三乙烯二胺 作用下， 20.0 ℃ 、1500.02 MPa 条件下， 反应 312.0h， 以69%的产率得到N-[(1RS,4SR,8RS)-6-acetyl-8-ethoxy-1-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-4-yl]benzamide
  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

• 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.