N-(6-(((bis(6-phenylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide | 1447733-09-6

• 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: N-(6-(((bis(6-phenylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide
• 英文别名: N-[6-[[bis(6-phenylpyridin-2-yl)methyl-(pyridin-2-ylmethyl)amino]methyl]pyridin-2-yl]-2,2-dimethylpropanamide
• CAS: 1447733-09-6
• 化学式: C₄₀H₃₈N₆O
• 分子量: 618.781
• InChiKey: NEPGKAMLRGOECO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 iron(II) tetrafluoroborate hexahydrate 、 N-(6-(((bis(6-phenylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到
  参考文献：
  名称：

  Secondary Coordination Sphere Influence on the Reactivity of Nonheme Iron(II) Complexes: An Experimental and DFT Approach

  摘要：

  The new biomimetic ligands N4Py(2Ph) (1) and N4Py(2Ph,amide) (2) were synthesized and yield the iron(II) complexes [Fe-II(N4Py(2Ph))(NCCH3)](BF4)(2) (3) and [Fe-II(N4Py(2Ph,amide))](BF4)(2) (5). Controlled orientation of the Ph substituents in 3 leads to facile triplet spin reactivity for a putative Fe-IV(O) intermediate, resulting in rapid arene hydroxylation. Addition of a peripheral amide substituent within hydrogen-bond distance of the iron first coordination sphere leads to stabilization of a high-spin (FeOOR)-O-III species which decays without arene hydroxylation. These results provide new insights regarding the impact of secondary coordination sphere effects at nonheme iron centers.

  DOI：

  10.1021/ja402688t
• 作为产物：
  描述：

  双(6-溴吡啶-2-基)甲酮 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 盐酸羟胺 、 sodium acetate 、 sodium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 150.0h， 生成 N-(6-(((bis(6-phenylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide
  参考文献：
  名称：

  Secondary Coordination Sphere Influence on the Reactivity of Nonheme Iron(II) Complexes: An Experimental and DFT Approach

  摘要：

  The new biomimetic ligands N4Py(2Ph) (1) and N4Py(2Ph,amide) (2) were synthesized and yield the iron(II) complexes [Fe-II(N4Py(2Ph))(NCCH3)](BF4)(2) (3) and [Fe-II(N4Py(2Ph,amide))](BF4)(2) (5). Controlled orientation of the Ph substituents in 3 leads to facile triplet spin reactivity for a putative Fe-IV(O) intermediate, resulting in rapid arene hydroxylation. Addition of a peripheral amide substituent within hydrogen-bond distance of the iron first coordination sphere leads to stabilization of a high-spin (FeOOR)-O-III species which decays without arene hydroxylation. These results provide new insights regarding the impact of secondary coordination sphere effects at nonheme iron centers.

  DOI：

  10.1021/ja402688t