[6-[(1R)-1-azidoethyl]pyridin-2-yl]methoxy-tert-butyl-dimethylsilane | 263718-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [6-[(1R)-1-azidoethyl]pyridin-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 263718-56-5
• 化学式: C₁₄H₂₄N₄OSi
• 分子量: 292.456
• InChiKey: XVNKXENIYCSKEP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [6-[(1R)-1-azidoethyl]pyridin-2-yl]methoxy-tert-butyl-dimethylsilane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到(1R)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanamine
  参考文献：
  名称：

  Synthesis of Optically Pure 1-(2-Pyridinyl)ethylamine and 4-(2-Pyridinyl)-1,3-oxazolin-2-one

  摘要：

  Several (R)-1-(2-pyridinyl)ethylamines (4) were prepared from (S)-1-(2-pyridinyl)ethanols (L) with complete inversion of the chiral center. Substitution of (S)-1-(2-pyridinyl)ethyl methanesulfonate (2) with sodium azide gave (R)-1-(2pyridinyl)ethyl azide (3) stereospecifically, and reduction of the azide afforded the corresponding amine (4) in good yield. When optically pure 2-silyloxy-1-(2-piridinyl)ethanol was used, 2-silyloxy-1-(2-pyridinyl)ethylamine was obtained, and this was converted to optically pure pyridine-substituted 1,3-oxazolidin-2-one at the 4-position.

  DOI：

  10.3987/com-99-s78
• 作为产物：
  描述：

  (1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanol 在 4-二甲氨基吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.67h， 生成 [6-[(1R)-1-azidoethyl]pyridin-2-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Synthesis of Optically Pure 1-(2-Pyridinyl)ethylamine and 4-(2-Pyridinyl)-1,3-oxazolin-2-one

  摘要：

  Several (R)-1-(2-pyridinyl)ethylamines (4) were prepared from (S)-1-(2-pyridinyl)ethanols (L) with complete inversion of the chiral center. Substitution of (S)-1-(2-pyridinyl)ethyl methanesulfonate (2) with sodium azide gave (R)-1-(2pyridinyl)ethyl azide (3) stereospecifically, and reduction of the azide afforded the corresponding amine (4) in good yield. When optically pure 2-silyloxy-1-(2-piridinyl)ethanol was used, 2-silyloxy-1-(2-pyridinyl)ethylamine was obtained, and this was converted to optically pure pyridine-substituted 1,3-oxazolidin-2-one at the 4-position.

  DOI：

  10.3987/com-99-s78

文献信息

• Synthesis of Optically Pure 1-(2-Pyridinyl)ethylamine and 4-(2-Pyridinyl)-1,3-oxazolin-2-one
  作者：Jun'ichi Uenishi、Takao Hiraoka、Kyoko Yuyama、Osamu Yonemitsu

  DOI：10.3987/com-99-s78

  日期：——

  Several (R)-1-(2-pyridinyl)ethylamines (4) were prepared from (S)-1-(2-pyridinyl)ethanols (L) with complete inversion of the chiral center. Substitution of (S)-1-(2-pyridinyl)ethyl methanesulfonate (2) with sodium azide gave (R)-1-(2pyridinyl)ethyl azide (3) stereospecifically, and reduction of the azide afforded the corresponding amine (4) in good yield. When optically pure 2-silyloxy-1-(2-piridinyl)ethanol was used, 2-silyloxy-1-(2-pyridinyl)ethylamine was obtained, and this was converted to optically pure pyridine-substituted 1,3-oxazolidin-2-one at the 4-position.