ethyl (E)-6-acetoxy-7-nitrooct-2-enoate | 902463-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-6-acetoxy-7-nitrooct-2-enoate
• 英文别名: ethyl (E)-6-acetyloxy-7-nitrooct-2-enoate
• CAS: 902463-93-8
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: HIVNTBNENFBDRL-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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)-6-acetoxy-7-nitrooct-2-enoate 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-methylcyclopentyl)acetate 、 ethyl (3-acetoxy-2-methylcyclopentyl)acetate 、 ethyl (3-acetoxy-2-methylcyclopentyl)acetate 、 ethyl (3-acetoxy-2-methylcyclopentyl)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：

  6-(tert-butyldimethylsilanyloxy)-2-nitrohexan-3-ol 在 吡啶 、 sodium hydroxide 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 ethyl (E)-6-acetoxy-7-nitrooct-2-enoate
  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