(3S,4R)-1-[2-[(3R,4S)-2-oxo-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-1-yl]ethyl]-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-2-one | 1234319-83-5

• 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)-1-[2-[(3R,4S)-2-oxo-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-1-yl]ethyl]-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-2-one
• CAS: 1234319-83-5
• 化学式: C₃₈H₃₆N₂O₆
• 分子量: 616.714
• InChiKey: IKWIFQMEUSESNM-IYMPVJEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 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)-1-[2-[(3R,4S)-2-oxo-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-1-yl]ethyl]-4-phenyl-3-(2-prop-2-enoxyphenoxy)azetidin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(1S,11E,22R,29R,30S)-29,30-diphenyl-2,9,14,21-tetraoxa-24,27-diazapentacyclo[25.1.1.122,24.03,8.015,20]triaconta-3,5,7,11,15,17,19-heptaene-23,28-dione
  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
• 作为产物：
  描述：

  N,N-双(苯基亚甲基)-1,2-乙二胺 、 o-allyloxyphenoxyacetyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以40%的产率得到
  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.