4-(tert-butyldimethylsilanyloxy)-1-(1-nitrocyclopentyl)butyl acetate | 902463-80-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-(tert-butyldimethylsilanyloxy)-1-(1-nitrocyclopentyl)butyl acetate
• 英文别名: [4-[Tert-butyl(dimethyl)silyl]oxy-1-(1-nitrocyclopentyl)butyl] acetate
• CAS: 902463-80-3
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: KFEPXPZUOVRYNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilanyloxy)-1-(1-nitrocyclopentyl)butyl acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到4-hydroxy-1-(1-nitrocyclopentyl)butyl 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：

  4-(叔丁基二甲基甲硅烷氧基)正丁醛 在 吡啶 、 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 4-(tert-butyldimethylsilanyloxy)-1-(1-nitrocyclopentyl)butyl 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