propyl 3,3-bis(1-methylbenzimidazol-2-yl)-propionate | 862211-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: propyl 3,3-bis(1-methylbenzimidazol-2-yl)-propionate
• 英文别名: propyl 3,3-bis(1-methylbenzimidazol-2-yl)propionate；Propyl 3,3-bis(1-methylbenzimidazol-2-yl)propanoate；propyl 3,3-bis(1-methylbenzimidazol-2-yl)propanoate
• CAS: 862211-19-6
• 化学式: C₂₂H₂₄N₄O₂
• 分子量: 376.458
• InChiKey: QTYAEBCSAIPOQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  propyl 3,3-bis(1-methylbenzimidazol-2-yl)-propionate 在 吡啶 、 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， 生成 3,3-bis(1-methylbenzimidazol-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
• 作为产物：
  描述：

  1-甲基-2-[(1-甲基苯并咪唑-2-基)甲基]苯并咪唑 、 溴乙酸丙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以92%的产率得到propyl 3,3-bis(1-methylbenzimidazol-2-yl)-propionate
  参考文献：
  名称：

  双(1-甲基咪唑-2-基)丙酸酯和双(1-甲基苯并咪唑-2-基)-丙酸酯：仿生N,N,寡配体的新家族——合成、结构和CuII配位配合物

  摘要：

  介绍了一种通向新的三齿、三足 N、N、O 配体的一般合成路线，该配体带有一个羧酸酯基团和两个生物相关的咪唑部分。这一新配体家族的母体化合物 A[MIm2Pr] (1) 和 A[BenzMIm2Pr] (2) (A = H、K、Bu4N) 分两步合成，总产率高。HMIm2Pr (1a) 和HBenzMIm2Pr (2a) 的结构通过X 射线晶体结构测定证实，两种分子形成无限的一维氢键链。合成路线允许微调两种配体系统的物理特性，例如溶解度和结晶的难易程度。研究了两种配体通过所有供体原子进行面配位的能力，并获得了 [CuL2] 类型的两种同构单核铜 (II) 配合物。[Cu(MIm2Pr)2]·2H2O (3) 和 [Cu(BenzMIm2Pr)2]·3.12(H2O)·1.74(C2H5OH) (4) 均已通过 X 射线晶体学、ESI-MS、元素分析、 UV/Vis、IR 和 EPR 光谱。在

  DOI：

  10.1002/ejic.200400830

文献信息

• Bis(1‐methylimidazol‐2‐yl)propionates and Bis(1‐methylbenzimidazol‐2‐yl)‐propionates: A New Family of Biomimetic <i>N</i> , <i>N</i> , <i>O</i> Ligands – Synthesis, Structures and Cu ^II Coordination Complexes
  作者：Pieter C. A. Bruijnincx、Martin Lutz、Anthony L. Spek,、Ernst E. van Faassen、Bert M. Weckhuysen、Gerard van Koten、Robertus J. M. Klein Gebbink

  DOI：10.1002/ejic.200400830

  日期：2005.2

  bonded chains. The synthetic route allows for the fine-tuning of the physical properties of both ligand systems, e.g., solubility and ease of crystallization. The capability of the two ligands to coordinate facially through all donor atoms was investigated and two isostructural mononuclear copper(II) complexes of the type [CuL2] were obtained. Both [Cu(MIm2Pr)2]·2H2O (3) and [Cu(BenzMIm2Pr)2]·3.12(H2O)·1

  介绍了一种通向新的三齿、三足 N、N、O 配体的一般合成路线，该配体带有一个羧酸酯基团和两个生物相关的咪唑部分。这一新配体家族的母体化合物 A[MIm2Pr] (1) 和 A[BenzMIm2Pr] (2) (A = H、K、Bu4N) 分两步合成，总产率高。HMIm2Pr (1a) 和HBenzMIm2Pr (2a) 的结构通过X 射线晶体结构测定证实，两种分子形成无限的一维氢键链。合成路线允许微调两种配体系统的物理特性，例如溶解度和结晶的难易程度。研究了两种配体通过所有供体原子进行面配位的能力，并获得了 [CuL2] 类型的两种同构单核铜 (II) 配合物。[Cu(MIm2Pr)2]·2H2O (3) 和 [Cu(BenzMIm2Pr)2]·3.12(H2O)·1.74(C2H5OH) (4) 均已通过 X 射线晶体学、ESI-MS、元素分析、 UV/Vis、IR 和 EPR 光谱。在
• Bioinspired Nonheme Iron Complexes Derived from an Extended Series of N,N,O-Ligated <b>BAIP</b> Ligands
  作者：Marcel A. H. Moelands、Sjoerd Nijsse、Emma Folkertsma、Bas de Bruin、Martin Lutz、Anthony L. Spek、Robertus J. M. Klein Gebbink

  DOI：10.1021/ic400096e

  日期：2013.7.1

  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.