6-(tert-butyldimethylsilanyloxy)-2-nitrohexan-3-ol | 902463-74-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-(tert-butyldimethylsilanyloxy)-2-nitrohexan-3-ol
• 英文别名: 6-[Tert-butyl(dimethyl)silyl]oxy-2-nitrohexan-3-ol
• CAS: 902463-74-5
• 化学式: C₁₂H₂₇NO₄Si
• 分子量: 277.436
• InChiKey: VWSSGIAOGFXVRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tert-butyldimethylsilanyloxy)-2-nitrohexan-3-ol 在 吡啶 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(1-nitroethyl)-4-oxobutyl 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：

  硝基乙烷 、 4-(叔丁基二甲基甲硅烷氧基)正丁醛 在 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到6-(tert-butyldimethylsilanyloxy)-2-nitrohexan-3-ol
  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

文献信息

• Radical-Induced Cyclopentannulation of Henry (Nitroaldol)-Derived Intermediates¹
  作者：Frederick A. Luzzio、Joel P. Ott、Damien Y. Duveau

  DOI：10.1021/jo0605546

  日期：2006.6.1

  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.