(S)-(1-oxy-pyridin-2-yl)-(1-oxy-pyridin-3-yl)-(1-oxy-pyridin-4-yl)-phenyl-methane | 1316713-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-(1-oxy-pyridin-2-yl)-(1-oxy-pyridin-3-yl)-(1-oxy-pyridin-4-yl)-phenyl-methane
• CAS: 1316713-34-4
• 化学式: C₂₂H₁₇N₃O₃
• 分子量: 371.395
• InChiKey: DLWOTQDTXWYTOZ-QFIPXVFZSA-N

反应信息

• 作为产物：
  描述：

  rac-(1-oxy-pyridin-2-yl)-(1-oxy-pyridin-3-yl)-(1-oxy-pyridin-4-yl)-phenyl-methane 在 Chiralcel OD 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 (S)-(1-oxy-pyridin-2-yl)-(1-oxy-pyridin-3-yl)-(1-oxy-pyridin-4-yl)-phenyl-methane 、 (R)-(1-oxy-pyridin-2-yl)-(1-oxy-pyridin-3-yl)-(1-oxy-pyridin-4-yl)-phenyl-methane
  参考文献：
  名称：

  “Marking” the nitrogen atoms of phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)-methane. Synthesis and absolute configuration of the corresponding tris(pyridine N-oxide)

  摘要：

  AbstractTo “mark” the nitrogen atoms in phenyl‐(2‐pyridyl)‐(3‐pyridyl)‐(4‐pyridyl)methane (1), we have synthesized the corresponding tris(pyridine N‐oxide) 2 by oxidation of 1 with m‐chloroperbenzoic acid. The nitrogen atoms of 2 are unequivocally determined by the X‐ray crystal analysis of a single crystal of rac-2 whereas the nitrogen atoms cannot be assigned at all in the case of rac-1. N‐Oxide 2 can be resolved by chiral high‐performance liquid chromatography under similar conditions to those used for the resolution of 1. The calculated circular dichroism (CD) curve for (R)-1 on the basis of time‐dependent density functional theory reproduces the experimental spectra very well to suggest that the second‐eluted fraction ([CD(+)283]‐2) is the R isomer, namely (R)‐[CD(+)283]‐2. The independent absolute configuration determinations for 1 and 2 are in keeping with the chemical correlation between the two compounds by oxidation of (R)-2 into (R)-1. Chirality 2011. © 2011 Wiley‐Liss, Inc.

  DOI：

  10.1002/chir.20965