ethyl (E)-3-[2-(1-acetoxy-2-nitropropyl)phenyl]acrylate | 902463-99-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-[2-(1-acetoxy-2-nitropropyl)phenyl]acrylate
• 英文别名: ethyl (E)-3-[2-(1-acetyloxy-2-nitropropyl)phenyl]prop-2-enoate
• CAS: 902463-99-4
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: CCJVWMUYVWWGIS-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[2-(1-acetoxy-2-nitropropyl)phenyl]acrylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 ethyl (3-acetoxy-2-methylindan-1-yl)acetate 、 ethyl (3-acetoxy-2-methylindan-1-yl)acetate
  参考文献：
  名称：

  Radical-Induced Cyclopentannulation of Henry (Nitroaldol)-Derived Intermediates¹

  摘要：

  Tributyltin hydride-mediated cyclizations of 1-nitro-2-acetoxy-5-hexenes 7a-g having multiple substitutions on carbons 1 and 6 result in 2,3-substituted-1-acetoxycyclopentanes 1a-g. The substrates were prepared by nitroaldol reactions of silyloxyaldehydes followed by acetylation, desilylation, and oxidation to the acetoxynitroaldehydes 6a-e. Wittig olefination of aldehydes 6a-e then afforded substrates for the radical cyclizations. The overall scheme gave a diverse array of cyclopentanes, including gem-disubstituted cyclopentanes having substitution on three contiguous carbons.

  DOI：

  10.1021/jo0605546
• 作为产物：
  描述：

  2-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde 在 吡啶 、 sodium hydroxide 、 pyridinium chlorochromate 、 三氟乙酸 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 ethyl (E)-3-[2-(1-acetoxy-2-nitropropyl)phenyl]acrylate
  参考文献：
  名称：

  Radical-Induced Cyclopentannulation of Henry (Nitroaldol)-Derived Intermediates¹

  摘要：

  Tributyltin hydride-mediated cyclizations of 1-nitro-2-acetoxy-5-hexenes 7a-g having multiple substitutions on carbons 1 and 6 result in 2,3-substituted-1-acetoxycyclopentanes 1a-g. The substrates were prepared by nitroaldol reactions of silyloxyaldehydes followed by acetylation, desilylation, and oxidation to the acetoxynitroaldehydes 6a-e. Wittig olefination of aldehydes 6a-e then afforded substrates for the radical cyclizations. The overall scheme gave a diverse array of cyclopentanes, including gem-disubstituted cyclopentanes having substitution on three contiguous carbons.

  DOI：

  10.1021/jo0605546