(6-bromo-2-pyridylmethyl)(6-fluoro-2-pyridylmethyl)(2-pyridylmethyl)amine | 1312775-62-4

• 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-bromo-2-pyridylmethyl)(6-fluoro-2-pyridylmethyl)(2-pyridylmethyl)amine
• 英文别名: FBrTPA；N-[(6-bromopyridin-2-yl)methyl]-1-(6-fluoropyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine
• CAS: 1312775-62-4
• 化学式: C₁₈H₁₆BrFN₄
• 分子量: 387.254
• InChiKey: PCNAZWKZNDSEBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-bromo-2-pyridylmethyl)(6-fluoro-2-pyridylmethyl)(2-pyridylmethyl)amine 、 iron(II) chloride 以 四氢呋喃 为溶剂， 以83%的产率得到FeCl2(FBrTPA)
  参考文献：
  名称：

  Asymmetry and steric hindrance in tripodal ligands: Reaching the limit for octahedral geometry with the newly synthesized [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod in FeCl2 complexes

  摘要：

  We have synthesized the fully unsymmetrical [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod FBrTPA. The synthesis involves preparation of the already known [(6-bromo 2-pyridylmethyl) (2-pyridylmethyl)] amine BrDPA, which is obtained either by classical condensation of a-substituted pyridine carboxaldehyde with aminomethyl pyridine, or by a pathway involving the protection/deprotection sequence of this primary amine. This second way is useful for syntheses of monosubstituted DPAs in the cases where a-substituted pyridine carboxaldehydes are unavailable. The crystal structure of the FeCl2 complex shows that the ligand binds in a kappa(4)-N fashion, with however relatively long ligand-to-metal distances. The spectroscopic and electrochemical studies support decoordination of the bromopyridyl substituent in solution, with kappa(3)-N coordination mode of the tripod within a complex displaying a trigonal bipyramidal geometry at the metal centre. This complex reacts easily with dry oxygen to yield an unsymmetrical mu-oxo diferric complex, the structure of which is also reported. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.04.015
• 作为产物：
  描述：

  6-溴吡啶-2-甲醛 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 30.0h， 生成 (6-bromo-2-pyridylmethyl)(6-fluoro-2-pyridylmethyl)(2-pyridylmethyl)amine
  参考文献：
  名称：

  Asymmetry and steric hindrance in tripodal ligands: Reaching the limit for octahedral geometry with the newly synthesized [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod in FeCl2 complexes

  摘要：

  We have synthesized the fully unsymmetrical [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod FBrTPA. The synthesis involves preparation of the already known [(6-bromo 2-pyridylmethyl) (2-pyridylmethyl)] amine BrDPA, which is obtained either by classical condensation of a-substituted pyridine carboxaldehyde with aminomethyl pyridine, or by a pathway involving the protection/deprotection sequence of this primary amine. This second way is useful for syntheses of monosubstituted DPAs in the cases where a-substituted pyridine carboxaldehydes are unavailable. The crystal structure of the FeCl2 complex shows that the ligand binds in a kappa(4)-N fashion, with however relatively long ligand-to-metal distances. The spectroscopic and electrochemical studies support decoordination of the bromopyridyl substituent in solution, with kappa(3)-N coordination mode of the tripod within a complex displaying a trigonal bipyramidal geometry at the metal centre. This complex reacts easily with dry oxygen to yield an unsymmetrical mu-oxo diferric complex, the structure of which is also reported. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.04.015

文献信息

• Asymmetry and steric hindrance in tripodal ligands: Reaching the limit for octahedral geometry with the newly synthesized [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod in FeCl2 complexes
  作者：Laila Benhamou、Hassen Jaafar、Aurore Thibon、Mohammed Lachkar、Dominique Mandon

  DOI：10.1016/j.ica.2011.04.015

  日期：2011.7

  We have synthesized the fully unsymmetrical [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine tripod FBrTPA. The synthesis involves preparation of the already known [(6-bromo 2-pyridylmethyl) (2-pyridylmethyl)] amine BrDPA, which is obtained either by classical condensation of a-substituted pyridine carboxaldehyde with aminomethyl pyridine, or by a pathway involving the protection/deprotection sequence of this primary amine. This second way is useful for syntheses of monosubstituted DPAs in the cases where a-substituted pyridine carboxaldehydes are unavailable. The crystal structure of the FeCl2 complex shows that the ligand binds in a kappa(4)-N fashion, with however relatively long ligand-to-metal distances. The spectroscopic and electrochemical studies support decoordination of the bromopyridyl substituent in solution, with kappa(3)-N coordination mode of the tripod within a complex displaying a trigonal bipyramidal geometry at the metal centre. This complex reacts easily with dry oxygen to yield an unsymmetrical mu-oxo diferric complex, the structure of which is also reported. (C) 2011 Elsevier B. V. All rights reserved.