1-(5-bromo-1-oxido-2-pyridinyl)propan-1-one | 1563017-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-bromo-1-oxido-2-pyridinyl)propan-1-one
• 英文别名: 1-(5-Bromo-1-oxidopyridin-1-ium-2-yl)propan-1-one；1-(5-bromo-1-oxidopyridin-1-ium-2-yl)propan-1-one
• CAS: 1563017-60-6
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: JUHRPGTWSGUPKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 1-(5-bromo-1-oxido-2-pyridinyl)propan-1-one 在 copper(II) bis(trifluoromethanesulfonate) 、 (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 73.0h， 以80%的产率得到1-nitromethyl-1-(5-bromo-1-oxido-2-pyridinyl)propan-1-ol
  参考文献：
  名称：

  Enantioselective Addition of Nitromethane to 2-Acylpyridine N-Oxides. Expanding the Generation of Quaternary Stereocenters with the Henry Reaction

  摘要：

  The direct asymmetric Henry reaction with prochiral ketones, leading to tertiary nitroaldols, is an elusive reaction so far limited to a reduced number of reactive substrates such as trifluoromethyl ketones or alpha-keto carbonyl compounds. Expanding the scope of this important reaction, the direct asymmetric addition of nitromethane to 2-acylpyridine N-oxides catalyzed by a BOX-Cu(II) complex to give the corresponding pyridine-derived tertiary nitroaldols having a quaternary stereogenic center with variable yields and good enantioselectivity, is described.

  DOI：

  10.1021/ol500082d
• 作为产物：
  描述：

  1-(5-bromopyridin-2-yl)propan-1-ol 在 草酰氯 、 二甲基亚砜 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1-(5-bromo-1-oxido-2-pyridinyl)propan-1-one
  参考文献：
  名称：

  Enantioselective Addition of Nitromethane to 2-Acylpyridine N-Oxides. Expanding the Generation of Quaternary Stereocenters with the Henry Reaction

  摘要：

  The direct asymmetric Henry reaction with prochiral ketones, leading to tertiary nitroaldols, is an elusive reaction so far limited to a reduced number of reactive substrates such as trifluoromethyl ketones or alpha-keto carbonyl compounds. Expanding the scope of this important reaction, the direct asymmetric addition of nitromethane to 2-acylpyridine N-oxides catalyzed by a BOX-Cu(II) complex to give the corresponding pyridine-derived tertiary nitroaldols having a quaternary stereogenic center with variable yields and good enantioselectivity, is described.

  DOI：

  10.1021/ol500082d

文献信息

• A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with difluorinated silyl enol ethers and acylpyridine <i>N</i>-oxides
  作者：Amparo Sanz-Marco、Daniel Esperilla、Marc Montesinos-Magraner、Carlos Vila、M. Carmen Muñoz、José R. Pedro、Gonzalo Blay

  DOI：10.1039/d2ob01763f

  日期：——

  A Cu(II)/BOX complex catalyses the enantioselective addition of difluorinated silyl enol ethers to acylpyridine N-oxides. The reaction provides difluorinated chiral tertiary alcohols of great interest in medicinal chemistry. These compounds are obtained in moderate to excellent yields and with high enantioselectivities. The stereochemical outcome of the reaction has been explained by DFT calculations

  Cu( II )/BOX 络合物催化二氟化甲硅烷基烯醇醚对映选择性加成酰基吡啶N-氧化物。该反应提供了在药物化学中具有重要意义的二氟化手性叔醇。这些化合物以中等到极好的产率和高对映体选择性获得。反应的立体化学结果已通过 DFT 计算得到解释。
• Enantioselective Addition of Nitromethane to 2-Acylpyridine <i>N</i>-Oxides. Expanding the Generation of Quaternary Stereocenters with the Henry Reaction
  作者：Melireth Holmquist、Gonzalo Blay、M. Carmen Muñoz、José R. Pedro

  DOI：10.1021/ol500082d

  日期：2014.2.21

  The direct asymmetric Henry reaction with prochiral ketones, leading to tertiary nitroaldols, is an elusive reaction so far limited to a reduced number of reactive substrates such as trifluoromethyl ketones or alpha-keto carbonyl compounds. Expanding the scope of this important reaction, the direct asymmetric addition of nitromethane to 2-acylpyridine N-oxides catalyzed by a BOX-Cu(II) complex to give the corresponding pyridine-derived tertiary nitroaldols having a quaternary stereogenic center with variable yields and good enantioselectivity, is described.