rac-phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)-methane | 1025794-53-9

• 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: rac-phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)-methane
• 英文别名: 2-(Phenyl-pyridin-3-yl-pyridin-4-ylmethyl)pyridine；2-(phenyl-pyridin-3-yl-pyridin-4-ylmethyl)pyridine
• CAS: 1025794-53-9
• 化学式: C₂₂H₁₇N₃
• 分子量: 323.397
• InChiKey: ORVPGZCJVWJBOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)-methane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到rac-(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