(3S,4R)-3-naphthalen-2-yloxy-1-[2-[(3R,4S)-3-naphthalen-2-yloxy-2-oxo-4-(2-prop-2-enoxyphenyl)azetidin-1-yl]ethyl]-4-(2-prop-2-enoxyphenyl)azetidin-2-one | 1158842-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R)-3-naphthalen-2-yloxy-1-[2-[(3R,4S)-3-naphthalen-2-yloxy-2-oxo-4-(2-prop-2-enoxyphenyl)azetidin-1-yl]ethyl]-4-(2-prop-2-enoxyphenyl)azetidin-2-one
• CAS: 1158842-78-4
• 化学式: C₄₆H₄₀N₂O₆
• 分子量: 716.833
• InChiKey: WBMQXEYPPPEIOR-QRJWCXHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-naphthalen-2-yloxy-1-[2-[(3R,4S)-3-naphthalen-2-yloxy-2-oxo-4-(2-prop-2-enoxyphenyl)azetidin-1-yl]ethyl]-4-(2-prop-2-enoxyphenyl)azetidin-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 生成 、 (2S,3R,10S,11R,20E)-3,10-dinaphthalen-2-yloxy-18,23-dioxa-5,8-diazapentacyclo[22.4.0.02,5.08,11.012,17]octacosa-1(28),12,14,16,20,24,26-heptaene-4,9-dione
  参考文献：
  名称：

  Staudinger Ketene−Imine Cycloaddition, RCM Approach to Macrocrocyclic Bisazetidinones

  摘要：

  Application of Staudinger ketene-imine cycloaddition reaction to bis-o-allyloxyarylideneamines afforded the corresponding bisallyloxyazetidinones; as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded the corresponding macrocyclic bisazetidinones in good yields. The cis-anti-cis bisazetidinones are readily identified by H-1 NMR using Eu(hfC)(3) chiral shift reagent.

  DOI：

  10.1021/jo9006392
• 作为产物：
  描述：

  compound 、 萘氧基-2-羰酰氯 以 二氯甲烷 为溶剂， 反应 0.5h， 以46%的产率得到(3R,4S)-3-naphthalen-2-yloxy-1-[2-[(3R,4S)-3-naphthalen-2-yloxy-2-oxo-4-(2-prop-2-enoxyphenyl)azetidin-1-yl]ethyl]-4-(2-prop-2-enoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Staudinger Ketene−Imine Cycloaddition, RCM Approach to Macrocrocyclic Bisazetidinones

  摘要：

  Application of Staudinger ketene-imine cycloaddition reaction to bis-o-allyloxyarylideneamines afforded the corresponding bisallyloxyazetidinones; as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded the corresponding macrocyclic bisazetidinones in good yields. The cis-anti-cis bisazetidinones are readily identified by H-1 NMR using Eu(hfC)(3) chiral shift reagent.

  DOI：

  10.1021/jo9006392

文献信息

• Staudinger Ketene−Imine Cycloaddition, RCM Approach to Macrocrocyclic Bisazetidinones
  作者：Yehia A. Ibrahim、Talal F. Al-Azemi、Mohamed D. Abd El-Halim、Elizabeth John

  DOI：10.1021/jo9006392

  日期：2009.6.5

  Application of Staudinger ketene-imine cycloaddition reaction to bis-o-allyloxyarylideneamines afforded the corresponding bisallyloxyazetidinones; as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded the corresponding macrocyclic bisazetidinones in good yields. The cis-anti-cis bisazetidinones are readily identified by H-1 NMR using Eu(hfC)(3) chiral shift reagent.