2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)-pyridine | 874776-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)-pyridine
• 英文别名: 2-(1-Ethyl-5-phenylpyrazol-3-yl)pyridine；2-(1-ethyl-5-phenylpyrazol-3-yl)pyridine
• CAS: 874776-25-7
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: STHFYGQBQMMPIE-UHFFFAOYSA-N

物化性质

• 沸点：
  408.8±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)-pyridine 在 AgBF₄ 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 cis-[Pd(2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)pyridine)2](BPh4)2
  参考文献：
  名称：

  Reaction of [MCl2(CH3CN)2] (M=Pd(II), Pt(II)) compounds with N1-alkylpyridylpyrazole-derived ligands

  摘要：

  Palladium(II) and platinum(II) complexes with N-alkylpyridylpyrazole-derived ligands, 2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)pyridine (L-1) and 2-(1-octyl-5-phenyl-1H-pyrazol-3-yl)pyridine (L-2), cis-[MCl2(L)] (M = Pd(II), Pt(II)), have been synthesised. Treatment of [PdCl2(L)] (L = L-1, L-2) with excess of ligand (L-1, L-2), pyridine (py) or triphenylphosphine (PPh3) in the presence of AgBF4 and NaBPh4 produced the following complexes: [Pd(L)(2)](BPh4)(2), [Pd(L)(PY)(2)](BPh4)(2) and [Pd(L)(PPh3)(2)](BPh4)(2). All complexes have been characterised by elemental analyses, conductivity, IR and NMR spectroscopies. The crystal structures of cis-[PdCl2(L-2)] (2) and CiS-[PtCl2(L-1)] (3) were determined by a single crystal X-ray diffraction method. In both complexes, the metal atom is coordinated by one pyrazole nitrogen, one pyridine nitrogen and two chlorine atoms in a distorted square-planar geometry. In complex 3, pi-pi stacking between pairs of molecules is observed. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2005.07.047
• 作为产物：
  描述：

  1-phenyl-3-pyridin-2-yl-propane-1,3-dione 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 50.0h， 生成 2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)-pyridine
  参考文献：
  名称：

  Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

  摘要：

  New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.085

文献信息

• New (η³-Allyl)palladium Complexes with Pyridylpyrazole Ligands:  Synthesis, Characterization, and Study of the Influence of N1 Substituents on the Apparent Allyl Rotation
  作者：Vanessa Montoya、Josefina Pons、Jordi García-Antón、Xavier Solans、Mercè Font-Bardía、Josep Ros

  DOI：10.1021/om070093u

  日期：2007.6.1

  The allylpalladium [Pd(eta(3)-C3H5)(L)](BF4) (L = L-1 (1), L-2 (2), L-3 (3), L-4 (4)) complexes with pyridylpyrazole ligands 2-(5-phenyl-1H-pyrazol-3-yl)pyridine (L-1), 2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)pyridine (L-2), 2-(1-octyl-5-phenyl)-1H-pyrazol-3-yl)pyridine (L-3), and 2-(5-phenyl-3-(pyridin-2-yl)pyrazol-1-yl)ethanol (L-4) were synthesized from the appropriate pyridylpyrazole ligand and [Pd(eta(3)-C3H5)Cl](2) in the presence of AgBF4. The cationic complex 1 was converted into the neutral complex 5 under basic conditions. These complexes were characterized, and the crystal and molecular structure of [Pd(eta(3)-C3H5)(L-2)](BF4) (2) was resolved by X-ray diffraction. Also, we have studied the apparent allyl rotation, observed as H-syn-H-syn and H-anti-H-anti interconversions. The influences of the solvent, the traces of water, and the N1 substituent have also been studied.
• Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study
  作者：Vanessa Montoya、Josefina Pons、Vicenç Branchadell、Josep Ros

  DOI：10.1016/j.tet.2005.09.085

  日期：2005.12

  New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. (c) 2005 Elsevier Ltd. All rights reserved.
• Reaction of [MCl2(CH3CN)2] (M=Pd(II), Pt(II)) compounds with N1-alkylpyridylpyrazole-derived ligands
  作者：Vanessa Montoya、Josefina Pons、Xavier Solans、Mercè Font-Bardia、Josep Ros

  DOI：10.1016/j.ica.2005.07.047

  日期：2006.1

  Palladium(II) and platinum(II) complexes with N-alkylpyridylpyrazole-derived ligands, 2-(1-ethyl-5-phenyl-1H-pyrazol-3-yl)pyridine (L-1) and 2-(1-octyl-5-phenyl-1H-pyrazol-3-yl)pyridine (L-2), cis-[MCl2(L)] (M = Pd(II), Pt(II)), have been synthesised. Treatment of [PdCl2(L)] (L = L-1, L-2) with excess of ligand (L-1, L-2), pyridine (py) or triphenylphosphine (PPh3) in the presence of AgBF4 and NaBPh4 produced the following complexes: [Pd(L)(2)](BPh4)(2), [Pd(L)(PY)(2)](BPh4)(2) and [Pd(L)(PPh3)(2)](BPh4)(2). All complexes have been characterised by elemental analyses, conductivity, IR and NMR spectroscopies. The crystal structures of cis-[PdCl2(L-2)] (2) and CiS-[PtCl2(L-1)] (3) were determined by a single crystal X-ray diffraction method. In both complexes, the metal atom is coordinated by one pyrazole nitrogen, one pyridine nitrogen and two chlorine atoms in a distorted square-planar geometry. In complex 3, pi-pi stacking between pairs of molecules is observed. (c) 2005 Elsevier B.V. All rights reserved.