4-[(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3,4-dihydroxypiperidin-2-ylidene]-2-(1-naphthyl)-4H-oxazol-5-one | 1254755-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3,4-dihydroxypiperidin-2-ylidene]-2-(1-naphthyl)-4H-oxazol-5-one
• CAS: 1254755-13-9
• 化学式: C₂₄H₂₂N₂O₈
• 分子量: 466.447
• InChiKey: WCNUYWFXMJDXDW-WMJVKIHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  134.96
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4-[(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3,4-isopropylidenedioxypiperidin-2-ylidene]-2-(1-naphthyl)-4H-oxazol-5-one 在 三氯化硼 、 水 、 碳酸氢钠 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 以42%的产率得到4-[(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3,4-dihydroxypiperidin-2-ylidene]-2-(1-naphthyl)-4H-oxazol-5-one
  参考文献：
  名称：

  Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit

  摘要：

  Epoxypiperidine derivatives bearing a dehydroamino acid unit were designed and synthesized as novel DNA alkylating agents based on the structure of azinomycins. A relaxation assay of plasmid DNA revealed that the epoxypiperidine derivative 3 has a DNA cleavage activity. Based on the studies, it would appear that the electron density of the amino group of epoxypiperidines plays a critically important role in the DNA cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.027