3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole | 3668-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole
• 英文别名: 3,5-Dimethyl-1-(3-phenoxypropyl)pyrazole
• CAS: 3668-98-2
• 化学式: C₁₄H₁₈N₂O
• mdl: MFCD19000439
• 分子量: 230.31
• InChiKey: FXWQJZOUSVKCRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯化镍二甲氧基乙烷 、 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole 以 二氯甲烷 为溶剂， 反应 24.0h， 以76%的产率得到NiCl₂{3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole}
  参考文献：
  名称：

  Nickel catalysts based on phenyl ether-pyrazol ligands: Synthesis, XPS study, and use in ethylene oligomerization

  摘要：

  A series of nickel(II) complexes bearing phenyl ether-pyrazol ligands [NiCl2L] (Ni1: L=3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole; Ni2: L=1-(3-phenoxypropyl)-3-phenyl-1H-pyrazole; Ni3: L=3,5-di-tert-butyl-1-(3-phenoxypropyl)-1H-pyrazole; Ni4: L=1-(3-phenoxypropyl)-1H-pyrazole) were synthesized and fully characterized by elemental analysis, high-resolution mass spectrometry (HRMS) and X-ray photoelectron spectroscopy (XPS). X-ray photoelectron data illustrates that the probability of (co)existing dimeric species increases in the following order: Ni4 < Ni1 < Ni2 < Ni3. All nickel precatalysts, activated with methylaluminoxane (MAO), exhibited moderate to high activities for ethylene oligomerization [TOF = 18.4-45.7 x 10(3) mol(ethylene)(mol(Ni))(-1) h(-1))] with good selectivities for 1-butene produced (62.6-80.7%). The ligand environment regarding the substituents on the pyrazolyl unit as well as the reaction parameters influence the catalytic performance and selectivity toward production of 1-butene. When activated with ethylaluminum sesquichloride (Et3Al2Cl3, EASC), Nil displayed low catalytic activity (TOF = 9300 (mol C2H4).(mol Ni-1 h(-1)); however, the 1-butene selectivity was increased, attaining 92.5%. The use of triphenylphosphine (PPh3) as auxiliary ligand afforded highly active catalyst system [TOF = 118.3 x 10(3) mol(ethylene)(mol(Ni))(-1) h(-1))] with poor selectivity for production of 1-butene (13.7%). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.12.031
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 3-苯氧基溴丙烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以64%的产率得到3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole
  参考文献：
  名称：

  Nickel catalysts based on phenyl ether-pyrazol ligands: Synthesis, XPS study, and use in ethylene oligomerization

  摘要：

  A series of nickel(II) complexes bearing phenyl ether-pyrazol ligands [NiCl2L] (Ni1: L=3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole; Ni2: L=1-(3-phenoxypropyl)-3-phenyl-1H-pyrazole; Ni3: L=3,5-di-tert-butyl-1-(3-phenoxypropyl)-1H-pyrazole; Ni4: L=1-(3-phenoxypropyl)-1H-pyrazole) were synthesized and fully characterized by elemental analysis, high-resolution mass spectrometry (HRMS) and X-ray photoelectron spectroscopy (XPS). X-ray photoelectron data illustrates that the probability of (co)existing dimeric species increases in the following order: Ni4 < Ni1 < Ni2 < Ni3. All nickel precatalysts, activated with methylaluminoxane (MAO), exhibited moderate to high activities for ethylene oligomerization [TOF = 18.4-45.7 x 10(3) mol(ethylene)(mol(Ni))(-1) h(-1))] with good selectivities for 1-butene produced (62.6-80.7%). The ligand environment regarding the substituents on the pyrazolyl unit as well as the reaction parameters influence the catalytic performance and selectivity toward production of 1-butene. When activated with ethylaluminum sesquichloride (Et3Al2Cl3, EASC), Nil displayed low catalytic activity (TOF = 9300 (mol C2H4).(mol Ni-1 h(-1)); however, the 1-butene selectivity was increased, attaining 92.5%. The use of triphenylphosphine (PPh3) as auxiliary ligand afforded highly active catalyst system [TOF = 118.3 x 10(3) mol(ethylene)(mol(Ni))(-1) h(-1))] with poor selectivity for production of 1-butene (13.7%). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.12.031

文献信息

• Chromium Complexes Supported by Phenyl Ether‐Pyrazolyl [N,O] Ligands as Catalysts for the Oligo‐ and Polymerization of Ethylene
  作者：Jorge L.S. Milani、Osvaldo L. Casagrande

  DOI：10.1002/aoc.5984

  日期：2020.12

  Cr2 and Cr3 showed moderate activity in ethylene oligomerization [TOF = 17,900–29,200 mol (ethylene)·mol (Cr)−1·h−1 at 80 °C] with Schultz‐Flory distribution of oligomers (K = 0.54–0.66) and production of polymer varying from 2.8 to 6.7 wt.%. On the other hand, under identical oligomerization conditions, Cr1/MAO behaved as a polymerization catalyst generating predominantly polyethylene (63.7 wt%).

  一系列新的Cr（III）配合物[Cr 1-（3-苯氧基丙基）-1H-吡唑} Cl 3 ] 2 （Cr1）， [Cr 1-（3-苯氧基丙基）-3,5-二甲基-1H合成了[吡唑} Cl 3 ] 2 （Cr2）和[Cr 1-（3-苯氧基丙基）-3-苯基-1H-吡唑} Cl 3 ] 2 （Cr3），并通过元素分析，高分辨率进行了表征质谱（HRMS）和红外光谱。在用甲基铝氧烷（MAO）活化后，铬预催化剂Cr2和Cr3在乙烯低聚中表现出中等活性[TOF = 17,900–29,200 mol（乙烯）·mol（Cr）-1 ·h -1在80°C下]，低聚物的舒尔茨-弗洛里分布（K = 0.54-0.66），聚合物的产量在2.8至6.7 wt。％之间变化。另一方面，在相同的低聚条件下，Cr1 / MAO充当聚合催化剂，主要产生聚乙烯（63.7重量％）。1-丁烯的含量是液体馏分中最大的组分，表明这些预催