1-naphthalen-1-yl-N-[2-[2-[2-(naphthalen-1-ylmethylideneamino)ethoxy]ethoxy]ethyl]methanimine | 169395-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthalen-1-yl-N-[2-[2-[2-(naphthalen-1-ylmethylideneamino)ethoxy]ethoxy]ethyl]methanimine
• CAS: 169395-30-6
• 化学式: C₂₈H₂₈N₂O₂
• 分子量: 424.543
• InChiKey: WFWBEDCUIYKXDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  o-allyloxyphenoxyacetyl chloride 、 1-naphthalen-1-yl-N-[2-[2-[2-(naphthalen-1-ylmethylideneamino)ethoxy]ethoxy]ethyl]methanimine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3R,4S)-4-naphthalen-1-yl-1-[2-[2-[2-[(2R,3S)-2-naphthalen-1-yl-4-oxo-3-(2-prop-2-enoxyphenoxy)azetidin-1-yl]ethoxy]ethoxy]ethyl]-3-(2-prop-2-enoxyphenoxy)azetidin-2-one 、
  参考文献：
  名称：

  Sequential Staudinger Ketene−Imine Cycloaddition, RCM Approach to Highly Rigid Macrocrocyclic Bisazetidinones

  摘要：

  An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene-imine cycloaddition of o-allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene-imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones 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 good yields of the corresponding novel macrocyclic bisazetidinones. The cis-anti-cis bisazetidinones are readily identified by (1)H NMR using Eu(hfc)(3) chiral shift reagent. (1)H NMR indicated the high shielding effect of the aryl substituents on one of the ortho-H's of the condensed phenylene ring, and VT (1)H NMR indicates the highly restricted rotation of the aryl groups, thus offering a highly rigid system.

  DOI：

  10.1021/jo100679d

文献信息

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

  DOI：10.1021/jo100679d

  日期：2010.7.2

  An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene-imine cycloaddition of o-allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene-imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones 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 good yields of the corresponding novel macrocyclic bisazetidinones. The cis-anti-cis bisazetidinones are readily identified by (1)H NMR using Eu(hfc)(3) chiral shift reagent. (1)H NMR indicated the high shielding effect of the aryl substituents on one of the ortho-H's of the condensed phenylene ring, and VT (1)H NMR indicates the highly restricted rotation of the aryl groups, thus offering a highly rigid system.