| 137743-63-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• CAS: 137743-63-6
• 化学式: C₇H₁₆NO₂
• 分子量: 146.21
• InChiKey: BJKNJLHAAIIINT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  13.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-硝基丙烷 在 二叔丁基过氧化物 、 三(三甲基硅基)硅烷 作用下， 以 苯 为溶剂， 生成 Diisopropyl-nitroxid 、 、 、
  参考文献：
  名称：

  Reactions of tris(trimethylsilyl)silyl radicals with nitro alkanes. EPR, kinetic, and product studies

  摘要：

  The radical-initiated reaction of tris(trimethylsilyl)silane with a variety of aliphatic nitro derivatives has been investigated. This silane, which for many applications is a valid alternative to tributyltin hydride, is unable to reduce tertiary nitroalkanes to the corresponding hydrocarbons. EPR results, as well as kinetic and products studies, have shown that this ''anomalous'' behavior is due to the fact that the nitroxide adducts formed by addition of tris(trimethylsilyl)silyl radicals to the nitro compounds fragment preferentially at the nitrogen-oxygen bond rather than at the carbon-nitrogen bond as in the analogous tributyltin adducts. The resulting silyloxy radical, (Me3Si)3SiO+, undergoes a fast rearrangement (k greater-than-or-equal-to 10(7) s-1 at room temperature) with migration of a Me3Si group from silicon to oxygen to give (Me3Si)2SiOSiMe3 which adds to the nitro compound affording a secondary nitroxide adduct. The kinetics of the decay of both primary and secondary adducts to nitromethane has been studied over a wide range of temperatures. With tertiary nitroalkanes persistent aminyl radicals, RNOSi(SiMe3)3, have also been detected.

  DOI：

  10.1021/jo00029a029

文献信息

• Reactions of tris(trimethylsilyl)silyl radicals with nitro alkanes. EPR, kinetic, and product studies
  作者：Marco Ballestri、Chryssostomos Chatgilialoglu、Marco Lucarini、Gian Franco Pedulli

  DOI：10.1021/jo00029a029

  日期：1992.1

  The radical-initiated reaction of tris(trimethylsilyl)silane with a variety of aliphatic nitro derivatives has been investigated. This silane, which for many applications is a valid alternative to tributyltin hydride, is unable to reduce tertiary nitroalkanes to the corresponding hydrocarbons. EPR results, as well as kinetic and products studies, have shown that this ''anomalous'' behavior is due to the fact that the nitroxide adducts formed by addition of tris(trimethylsilyl)silyl radicals to the nitro compounds fragment preferentially at the nitrogen-oxygen bond rather than at the carbon-nitrogen bond as in the analogous tributyltin adducts. The resulting silyloxy radical, (Me3Si)3SiO+, undergoes a fast rearrangement (k greater-than-or-equal-to 10(7) s-1 at room temperature) with migration of a Me3Si group from silicon to oxygen to give (Me3Si)2SiOSiMe3 which adds to the nitro compound affording a secondary nitroxide adduct. The kinetics of the decay of both primary and secondary adducts to nitromethane has been studied over a wide range of temperatures. With tertiary nitroalkanes persistent aminyl radicals, RNOSi(SiMe3)3, have also been detected.