(+)-cis-2-(3-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate | 817207-94-6

• 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: (+)-cis-2-(3-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate
• CAS: 817207-94-6
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: JBIMSHDQPXYDBH-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-cis-2-(3-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate 在 咪唑 、 氢氧化钾 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.5h， 生成 (3R,4S)-4-(3-(benzyloxy)phenyl)-3-TIPS-azetidin-2-one
  参考文献：
  名称：

  Syntheses and bioactivities of macrocyclic paclitaxel bis-lactones

  摘要：

  Five macrocyclic paclitaxel bis-lactones and their corresponding open chain taxoids were synthesized as models of the tubulin-binding conformation of paclitaxel. Macrocyclic lactones with a 19-21-membered ring underwent isomerization to form smaller rings. The lactones were evaluated for cytotoxicity and tubulin-polymerization ability. All five macrocyclic paclitaxel lactones were active, but less so than paclitaxel, while the rearranged macrocyclic lactones and the corresponding open-chain taxoids were much less active or inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.002
• 作为产物：
  描述：

  在 lipase PS₃₀ 、 三乙胺 作用下， 以 phosphate buffer 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 168.0h， 生成 (+)-cis-2-(3-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate
  参考文献：
  名称：

  Syntheses and bioactivities of macrocyclic paclitaxel bis-lactones

  摘要：

  Five macrocyclic paclitaxel bis-lactones and their corresponding open chain taxoids were synthesized as models of the tubulin-binding conformation of paclitaxel. Macrocyclic lactones with a 19-21-membered ring underwent isomerization to form smaller rings. The lactones were evaluated for cytotoxicity and tubulin-polymerization ability. All five macrocyclic paclitaxel lactones were active, but less so than paclitaxel, while the rearranged macrocyclic lactones and the corresponding open-chain taxoids were much less active or inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.002