(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine | 1254755-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine
• CAS: 1254755-07-1
• 化学式: C₂₆H₂₈N₂O₁₁S
• 分子量: 576.581
• InChiKey: VLMOXWXADQNEOW-FNRJOTQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  174.84
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine 在 甲醇 、 potassium carbonate 作用下， 反应 4.5h， 以44%的产率得到(3R,4R,5R)-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine
  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
• 作为产物：
  描述：

  (3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-3,4-dihydroxypiperidine 、 甲基磺酰氯 在 吡啶 作用下， 反应 1.0h， 以220 mg的产率得到(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine
  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