tert-butyl 3-(acrylamido)-1H-pyrazole-1-carboxylate | 1620562-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 3-(acrylamido)-1H-pyrazole-1-carboxylate
• 英文别名: Tert-butyl 3-(prop-2-enoylamino)pyrazole-1-carboxylate
• CAS: 1620562-48-2
• 化学式: C₁₁H₁₅N₃O₃
• 分子量: 237.258
• InChiKey: ZODHYYFBIBTDJT-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-C-(diethoxyphosphoryl)nitrone 、 tert-butyl 3-(acrylamido)-1H-pyrazole-1-carboxylate 以 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到diethyl trans-5-(1-(tert-butoxycarbonyl)-1H-pyrazol-3-ylcarbamoyl)-2-methylisoxazolidin-3-yl-3-phosphonate
  参考文献：
  名称：

  Novel 5-Arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates as Nucleotide Analogues

  摘要：

  A series of 5-substituted 3-phosphonylated isoxazolidines have been obtained via cycloaddition of N-methyl-C-(diethoxyphosphoryl)nitrone with N-heteroaromatic acrylamides. Good trans/cis diastereoselectivities (d.e. 58-76%) of isomeric (3-diethoxyphosphoryl)isoxazolidines were observed. cis- and trans-Isoxazolidine phosphonates were evaluated for their antiviral activity against a broad range of DNA and RNA viruses but were found inactive. Their cytostatic activity toward L1210, CEM, and HeLa cells was also established, and compounds cis-12r and trans-11r having a 2,2-difluorobenzo[d][1,3]dioxole moiety slightly inhibited proliferation of HeLa cells at IC50 values of 186 and 179 μM, respectively.

  DOI：

  10.1080/15257770.2014.909046
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 tert-butyl 3-(acrylamido)-1H-pyrazole-1-carboxylate
  参考文献：
  名称：

  Novel 5-Arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates as Nucleotide Analogues

  摘要：

  A series of 5-substituted 3-phosphonylated isoxazolidines have been obtained via cycloaddition of N-methyl-C-(diethoxyphosphoryl)nitrone with N-heteroaromatic acrylamides. Good trans/cis diastereoselectivities (d.e. 58-76%) of isomeric (3-diethoxyphosphoryl)isoxazolidines were observed. cis- and trans-Isoxazolidine phosphonates were evaluated for their antiviral activity against a broad range of DNA and RNA viruses but were found inactive. Their cytostatic activity toward L1210, CEM, and HeLa cells was also established, and compounds cis-12r and trans-11r having a 2,2-difluorobenzo[d][1,3]dioxole moiety slightly inhibited proliferation of HeLa cells at IC50 values of 186 and 179 μM, respectively.

  DOI：

  10.1080/15257770.2014.909046