(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine | 1254754-99-8

• 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-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine
• CAS: 1254754-99-8
• 化学式: C₂₉H₃₃N₃O₁₀S
• 分子量: 615.661
• InChiKey: DLJIRASYDLQMHY-DPRNDHLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  168.85
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4-methanesulfonyloxypiperidine 在 甲醇 、 potassium carbonate 作用下， 反应 4.5h， 以58%的产率得到(3R,4R,5R)-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-(1-pyrrolidinyl)carbonyl-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-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-3,4-dihydroxypiperidine 、 甲基磺酰氯 在 吡啶 作用下， 反应 2.0h， 以380 mg的产率得到(3R,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-(1-pyrrolidinyl)carbonyl-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