3,3-bis(1-methylimidazol-2-yl)-N-propylpropanamide | 1442662-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,3-bis(1-methylimidazol-2-yl)-N-propylpropanamide
• CAS: 1442662-57-8
• 化学式: C₁₄H₂₁N₅O
• 分子量: 275.354
• InChiKey: NRMANUSOKSUZKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iron(II) trifluoromethanesulfonate acetonitrile disolvate 、 3,3-bis(1-methylimidazol-2-yl)-N-propylpropanamide 以 乙腈 为溶剂， 生成 [Fe(BMIP^AnPr)₂](OTf)₂
  参考文献：
  名称：

  Bioinspired Nonheme Iron Complexes Derived from an Extended Series of N,N,O-Ligated BAIP Ligands

  摘要：

  A series of mononuclear Fe(II) triflate complexes based on the 3,3-bis(1-alkylimidazole-2-yl)propionate ester (BAIP) ligand scaffold are reported. I, these complexes, the tripodal N,N,O-BAIP ester ligand is varied by (i) changing the ester moiety (i.e., n-Pr, tert-Bu esters, n-Pr amide), (ii) changing the methylimidazole moieties to methylbenzimidazole moieties, and (iii) changing the methylimidazole moieties to 1-ethyl-4-isopropylimidazole moieties. The general structure of the resulting complexes comprises two facially capping BAIP ligands around a coordinatively saturated octahedral Fe(II) center, with either a transoid or cisoid orientation of the N,N,O-donor manifold that depends on the combined steric and electronic demand of the ligands, In the ligands. In the case of the sterically most encumbered ligand, a four-coordinate all N-coordinate complex is formed as well, which cocrystallizes with the six-coordinate complex. In combination with the catalytic properties of the new complexes in the epoxidation/cis-dihydroxylation of cyclooctene with H2O2, in terms of turnover number and cis-diol formation, these studies provide a number of insights for further ligand design and catalyst development aimed at Fe-mediated cis-dihydroxylation.

  DOI：

  10.1021/ic400096e
• 作为产物：
  描述：

  1-甲基-2-[(1-甲基咪唑-2-基)甲基]咪唑 在 吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 3,3-bis(1-methylimidazol-2-yl)-N-propylpropanamide
  参考文献：
  名称：

  Bioinspired Nonheme Iron Complexes Derived from an Extended Series of N,N,O-Ligated BAIP Ligands

  摘要：

  A series of mononuclear Fe(II) triflate complexes based on the 3,3-bis(1-alkylimidazole-2-yl)propionate ester (BAIP) ligand scaffold are reported. I, these complexes, the tripodal N,N,O-BAIP ester ligand is varied by (i) changing the ester moiety (i.e., n-Pr, tert-Bu esters, n-Pr amide), (ii) changing the methylimidazole moieties to methylbenzimidazole moieties, and (iii) changing the methylimidazole moieties to 1-ethyl-4-isopropylimidazole moieties. The general structure of the resulting complexes comprises two facially capping BAIP ligands around a coordinatively saturated octahedral Fe(II) center, with either a transoid or cisoid orientation of the N,N,O-donor manifold that depends on the combined steric and electronic demand of the ligands, In the ligands. In the case of the sterically most encumbered ligand, a four-coordinate all N-coordinate complex is formed as well, which cocrystallizes with the six-coordinate complex. In combination with the catalytic properties of the new complexes in the epoxidation/cis-dihydroxylation of cyclooctene with H2O2, in terms of turnover number and cis-diol formation, these studies provide a number of insights for further ligand design and catalyst development aimed at Fe-mediated cis-dihydroxylation.

  DOI：

  10.1021/ic400096e