(3S,4S,5R)-5-acetoxy-3,4-isopropylidenedioxy-2-methylthio-3,4,5,6-tetrahydropyridine | 1254754-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R)-5-acetoxy-3,4-isopropylidenedioxy-2-methylthio-3,4,5,6-tetrahydropyridine
• 英文别名: [(3aS,7R,7aS)-2,2-dimethyl-4-methylsulfanyl-3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-7-yl] acetate
• CAS: 1254754-72-7
• 化学式: C₁₁H₁₇NO₄S
• 分子量: 259.326
• InChiKey: XDNOXKOOMYBLGU-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1-naphthyl)-4H-oxazol-5-one 、 (3S,4S,5R)-5-acetoxy-3,4-isopropylidenedioxy-2-methylthio-3,4,5,6-tetrahydropyridine 以 甲苯 为溶剂， 反应 36.0h， 生成 4-[(3R,4S,5R)-5-acetoxy-3,4-isopropylidenedioxypiperidin-2-ylidene]-2-(1-naphthyl)-4H-oxazol-5-one 、 4-[(3R,4S,5R)-5-acetoxy-3,4-isopropylidenedioxypiperidin-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
• 作为产物：
  描述：

  (3S,4S,5R)-5-acetoxy-3,4-isopropylidenedioxypiperidine-2-thione 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到(3S,4S,5R)-5-acetoxy-3,4-isopropylidenedioxy-2-methylthio-3,4,5,6-tetrahydropyridine
  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

文献信息

• Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit
  作者：Takao Yamaguchi、Yuji Kawada、Satoshi Obika、Takeshi Imanishi、Kazuyuki Miyashita

  DOI：10.1016/j.tet.2010.08.027

  日期：2010.10

  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.