1,3-bis(3,5-dimethylpyrazol-2-ylmethyl)-2,3-dihydro-1H-perimidine | 1372138-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis(3,5-dimethylpyrazol-2-ylmethyl)-2,3-dihydro-1H-perimidine
• 英文别名: 1,3-bis[(3,5-dimethylpyrazol-1-yl)methyl]-2H-perimidine
• CAS: 1372138-48-1
• 化学式: C₂₃H₂₆N₆
• 分子量: 386.5
• InChiKey: CLRINXJCRVSOSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 1,3-bis(3,5-dimethylpyrazol-2-ylmethyl)-2,3-dihydro-1H-perimidine 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Monomeric Pd(II) complexes with trans-chelated pyrazole ligands as effective pre-catalysts for Heck cross-coupling reaction under mild aerobic conditions

  摘要：

  A new family of mononuclear palladium(II) complexes with bidentate trans-chelating pyrazole ligands [PdCl2(L-R)] (R = H, 1; Et, 2; Ph, 3; CHPh2, 4), where new ligand L-Et = 2-ethyl-1,3-bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-2,3-dihydro-1H-perimidine, and a new mononuclear palladium(II) complex with monodentate trans-chelated pyrazole ligand [PdCl2(Ph-pz')(2)] (5), where Ph-pz' = 3,5-dimethyl-1-phenyl-1H-pyrazole, have been synthesized and characterized. Complexes 2-5 were also structurally confirmed by single crystal X-ray diffraction analysis. Remarkably, under very mild conditions (65-70 degrees C), complex 4 appeared to be an active pre-catalyst for the Heck coupling reactions of iodobenzene and t-butyl acrylate in MeOH. In the presence of co-catalyst [nNBu(4)]Br, however, complex 5 displayed the highest catalytic activity for the Heck reactions of activated bromobenzene and t-butyl acrylate. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.08.016

文献信息

• Steric-influenced fluxionality in monomeric two and three coordinate copper(I) complexes with a trans-chelating bis-pyrazole ligand
  作者：Chang-Chuan Chou、Hsueh-Ju Liu、Lucas Hung-Chieh Chao、Hong-Bin Syu、Ting-Shen Kuo

  DOI：10.1016/j.poly.2012.02.012

  日期：2012.4

  upon the fluxional behavior of individual two and three coordinate copper(I)–pyrazole complexes, in comparison with the rigid three coordinate copper(I) complex [Cu(LPh)I] (2) and dynamic two coordinate copper(I) complex [Cu(LPh)](ClO4) (1·ClO4) found previously [17]. To the best of our knowledge, complex 5 represents the first example of a dynamic monomeric three coordinate copper(I) complex.

  两个新的反螯合 双吡唑基配体L H，其中L H = 1,3-双-（3,5-二甲基-吡唑-1-基甲基）-2,3-二氢-1 H-  亚氨基吡啶，L CHPh 2 LCHPh2 ，其中L CHPh 2 = 2-苯甲酰基-1,3-双-（3,5-二甲基-吡唑-1-基甲基）-2,3-二氢-1H-嘧啶LCHPh2 = 2-苯甲酰基-1,3-双-（3,5-二甲基-吡唑-1-基甲基）-2,3-二氢-1H-亚氨基im ，以及它们的两个和三个配位的铜（I）衍生物[Cu（L H）]（ClO 4）（3 · ClO 4），[Cu（L CHPh 2）]（ClO 4）[Cu（LCHPh2）]（ClO4）（4 ·ClO制备[ 4 ]和[Cu（L H）I]（5）并通过X射线晶体学对其结构进行表征。1 H NMR可变温度光谱显示，配合物4 ·ClO 4是刚性的，而配合物3 ·ClO 4和5在CH 2 Cl 2溶液中是非刚性的。
• Monomeric Pd(II) complexes with trans-chelated pyrazole ligands as effective pre-catalysts for Heck cross-coupling reaction under mild aerobic conditions
  作者：Chang-Chuan Chou、Chia-Chi Yang、Hong-Bin Syu、Ting-Shen Kuo

  DOI：10.1016/j.jorganchem.2013.08.016

  日期：2013.11

  A new family of mononuclear palladium(II) complexes with bidentate trans-chelating pyrazole ligands [PdCl2(L-R)] (R = H, 1; Et, 2; Ph, 3; CHPh2, 4), where new ligand L-Et = 2-ethyl-1,3-bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-2,3-dihydro-1H-perimidine, and a new mononuclear palladium(II) complex with monodentate trans-chelated pyrazole ligand [PdCl2(Ph-pz')(2)] (5), where Ph-pz' = 3,5-dimethyl-1-phenyl-1H-pyrazole, have been synthesized and characterized. Complexes 2-5 were also structurally confirmed by single crystal X-ray diffraction analysis. Remarkably, under very mild conditions (65-70 degrees C), complex 4 appeared to be an active pre-catalyst for the Heck coupling reactions of iodobenzene and t-butyl acrylate in MeOH. In the presence of co-catalyst [nNBu(4)]Br, however, complex 5 displayed the highest catalytic activity for the Heck reactions of activated bromobenzene and t-butyl acrylate. (C) 2013 Elsevier B. V. All rights reserved.