1,2-bis(6-methylpyridine-2-carboxamide)-4,5-dimethylbenzene | 916442-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-bis(6-methylpyridine-2-carboxamide)-4,5-dimethylbenzene
• 英文别名: 1,2-bis(6-methylpyridine-2-carboxamido)-4,5-dimethylbenzene；H26-Me2-Me2bpb；N-[4,5-dimethyl-2-[(6-methylpyridine-2-carbonyl)amino]phenyl]-6-methylpyridine-2-carboxamide
• CAS: 916442-80-3
• 化学式: C₂₂H₂₂N₄O₂
• 分子量: 374.442
• InChiKey: QHARFPAWFALNTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 1,2-bis(6-methylpyridine-2-carboxamide)-4,5-dimethylbenzene 以 甲醇 为溶剂， 以48%的产率得到Cu(6-Me2-Me2bpb)
  参考文献：
  名称：

  Steric effect on construction of Cu(II) complexes with pyridine carboxamide ligands

  摘要：

  The structures of three new Cu(II) complexes with pyridine carboxamide ligands (Me(2)bpb, 6-Me-2-Mebpb, and 6-Me-2-Me(2)bpb) have been determined. 6-Methyl-substituted pyridyl bpb ligands produced dimeric compounds with Cu(II) ions, and weak interactions between dimers can make even polymeric compounds, while bpb ligands without 6-methyl substitution produced monomeric Cu(II) complexes. The large distortion effects of 6-methyl-substitution are shown in Cu(II) complexes with 6-methyl-substituted pyridyl bpb ligands. This result suggests that the steric effect of 6-methyl-substitution plays important role for distortion of the structure, and 6-methyl-substitution can also influence to make polymeric compounds with interactions between Cu(II) ions and neighbor carbonyl oxygen atoms. In addition, the voltammetric behaviors of the Cu complexes were examined and classified into two groups, with/without 6-methyl group. The complexes without 6-methyl group show reversible redox waves at similar to-1.6 V, and the complexes with 6-methyl group do irreversible redox ones at similar to-1.3 V, indicating that the presence of the methyl group of 6-position of the complex makes the reduction of the complexes easier. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2007.10.006
• 作为产物：
  描述：

  6-甲基-2-吡啶甲酸 、 4，5-二甲基-1，2-苯二胺 在 吡啶 、 亚磷酸三苯酯 作用下， 生成 1,2-bis(6-methylpyridine-2-carboxamide)-4,5-dimethylbenzene
  参考文献：
  名称：

  四齿镍 (II) 和钯 (II) 配合物对降冰片烯乙烯基聚合的空间和电子效应

  摘要：

  一系列带有 N4 型四齿配体的 Ni(II) 和 Pd(II) 配合物，[Ni(-6-) 1] 和 [Pd(-6-) 2]；6- = N,N'-(o-phenylene)bis(6-methylpyridine-2-carboxamidate), = Cl, H, or , = , Cl, F, H, , or ) 被设计、合成和表征为研究配体对降冰片烯聚合催化剂的电子和空间效应。使用改性甲基铝氧烷作为活化剂，配合物对降冰片烯的聚合表现出较高的催化活性，镍配合物表现出比钯配合物更好的催化活性。苯环上带有基团的Ni配合物1a表现出最高的催化活性（g PNBEs/）和分子量（g/mol）PDI 100 ），并且比具有给电子基团的Ni配合物倾向于提供更高的聚合产率。获得了在卤代芳族溶剂中具有良好溶解性的无定形聚降冰片烯。已经提出了用于催化聚合的乙烯基加成机理。

  DOI：

  10.5012/bkcs.2011.32.6.1884

文献信息

• Pd(II) polymeric compounds directed by intermolecular C–H⋯X–C interactions (X=F, Cl): Suzuki–Miyaura cross-coupling catalytic activity by a novel N4-type saturated Pd complex
  作者：Jung Hwan Lee、Hee Jin Kim、Yun Wee Choi、Young Min Lee、Byeong Kwon Park、Cheal Kim、Sung-Jin Kim、Youngmee Kim

  DOI：10.1016/j.poly.2006.11.020

  日期：2007.5

  palladium polymeric compounds containing novel tetradentate halogen-substituted 6Me2bpX2− ligands (6Me2bpX2− = 1,2-bis(6-methylpyridine-2-carboxamide) halobenzene dianion, X = F for 4, Cl for 5) were constructed by non-classical C–H⋯X–C interactions, and the novel catalyst 5 was used to carry out Suzuki coupling reactions with aryl iodides and aryl boronic acids under mild conditions.

  摘要用非结构化方法构建了含有新型四齿卤素取代的6Me2bpX2-配体（6Me2bpX2- = 1,2-双（6-甲基吡啶-2-羧酰胺）卤代苯二阴离子，X = F代表4，Cl代表5）的新型钯聚合物。经典的C–H⋯X–C相互作用，并且使用新型催化剂5在温和的条件下与芳基碘化物和芳基硼​​酸进行Suzuki偶联反应。
• Steric effect on construction of Cu(II) complexes with pyridine carboxamide ligands
  作者：Do Nam Lee、Ji Young Ryu、Han Kwak、Young Min Lee、Sun Hwa Lee、Jung In Poong、Junghyun Lee、Woonsup Shin、Cheal Kim、Sung-Jin Kim、Youngmee Kim

  DOI：10.1016/j.molstruc.2007.10.006

  日期：2008.8

  The structures of three new Cu(II) complexes with pyridine carboxamide ligands (Me(2)bpb, 6-Me-2-Mebpb, and 6-Me-2-Me(2)bpb) have been determined. 6-Methyl-substituted pyridyl bpb ligands produced dimeric compounds with Cu(II) ions, and weak interactions between dimers can make even polymeric compounds, while bpb ligands without 6-methyl substitution produced monomeric Cu(II) complexes. The large distortion effects of 6-methyl-substitution are shown in Cu(II) complexes with 6-methyl-substituted pyridyl bpb ligands. This result suggests that the steric effect of 6-methyl-substitution plays important role for distortion of the structure, and 6-methyl-substitution can also influence to make polymeric compounds with interactions between Cu(II) ions and neighbor carbonyl oxygen atoms. In addition, the voltammetric behaviors of the Cu complexes were examined and classified into two groups, with/without 6-methyl group. The complexes without 6-methyl group show reversible redox waves at similar to-1.6 V, and the complexes with 6-methyl group do irreversible redox ones at similar to-1.3 V, indicating that the presence of the methyl group of 6-position of the complex makes the reduction of the complexes easier. (C) 2007 Elsevier B.V. All rights reserved.
• Steric and Electronic Effects of Tetradentate Nickel(II) and Palladium(II) Complexes toward the Vinyl Polymerization of Norbornene
  作者：Dong-Hwan Lee、Jung-Hwan Lee、Geun-Hee Eom、Hyo-Geun Koo、Cheal Kim、Ik-Mo Lee

  DOI：10.5012/bkcs.2011.32.6.1884

  日期：2011.6.20

  A series of Ni(II) and Pd(II) complexes bearing N4-type tetradentate ligands, [Ni(-6-) 1] and [Pd(-6-) 2]; 6- = N,N'-(o-phenylene)bis(6-methylpyridine-2-carboxamidate), = Cl, H, or , = , Cl, F, H, , or ) were designed, synthesized, and characterized to investigate electronic and steric effects of ligand on the norbornene polymerization catalysts. Using modified methylaluminoxanes as an activator, the

  一系列带有 N4 型四齿配体的 Ni(II) 和 Pd(II) 配合物，[Ni(-6-) 1] 和 [Pd(-6-) 2]；6- = N,N'-(o-phenylene)bis(6-methylpyridine-2-carboxamidate), = Cl, H, or , = , Cl, F, H, , or ) 被设计、合成和表征为研究配体对降冰片烯聚合催化剂的电子和空间效应。使用改性甲基铝氧烷作为活化剂，配合物对降冰片烯的聚合表现出较高的催化活性，镍配合物表现出比钯配合物更好的催化活性。苯环上带有基团的Ni配合物1a表现出最高的催化活性（g PNBEs/）和分子量（g/mol）PDI 100 ），并且比具有给电子基团的Ni配合物倾向于提供更高的聚合产率。获得了在卤代芳族溶剂中具有良好溶解性的无定形聚降冰片烯。已经提出了用于催化聚合的乙烯基加成机理。