2-(5-phenyl-3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethanol | 944163-00-2

• 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-(5-phenyl-3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethanol
• 英文别名: 2-(5-phenyl-3-(pyridyn-2-yl)-1H-pyrazol-1-yl)ethanol；2-(5-phenyl-3-(pyridin-2-yl)pyrazol-1-yl)ethanol；2-(5-Phenyl-3-pyridin-2-ylpyrazol-1-yl)ethanol
• CAS: 944163-00-2
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: HETIHBSGQUZFNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(acetonitrile)dichloroplatinum(II) 、 2-(5-phenyl-3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethanol 以 乙腈 为溶剂， 以56%的产率得到(2-(5-phenyl-3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethanol)dichloridoplatinum(II)
  参考文献：
  名称：

  Preparation, separation and characterisation of two regioisomers of a N-hydroxyalkylpyridylpyrazole ligand: A structural investigation of their coordination to Pd(II), Pt(II) and Zn(II) centres

  摘要：

  The reaction of the beta-diketone 1-phenyl-3-(pyridyn-2-yl)propane-1,3-dione, and the monosubstituted hydrazine 2-hydroxyethylhydrazine has been investigated. Two regioisomers were identified, 2-(3-phenyl-5-(pyridyn-2-yl)-1H-pyrazol-1-yl)ethanol (pzol.1) and 2-(5-phenyl-3-(pyridyn-2-yl)-1H-pyrazol-1-yl) ethanol (pzol.2) in 57:43 ratio. The separation of the regioisomers was done by silica column chromatography using ethyl acetate as eluent.Palladium(II) and platinum(II), [MCl2(pzol.1)(2)], [MCl2(pzol.2)], and zinc(II), [ZnCl2(pzol.1)], [ZnCl2(pzol.2)] complexes were synthesised and characterised. The crystals and molecular structures of [PdCl2(pzol.2)]center dot H2O and [ZnCl2(pzol.2)] were solved by X-ray diffraction, and consist of mononuclear complexes. In complex [PdCl2(pzol.2)]center dot H2O, the Pd(II) centre has a typical square planar geometry, with a slight tetrahedral distortion. The tetra-coordinated atom is bonded to one pyridinic nitrogen, one pyrazolic nitrogen and two chlorine atoms in cis disposition. The pzol.2 ligand acts as a bidentate chelate forming a five-membered metallocycle ring. In complex [ZnCl2(pzol.2)], the Zn(II) is five-coordinated with two Zn-N bonds (Zn-N-pz and Zn-N-py), one Zn-OH bond and two Zn-Cl bonds. The coordination geometry is intermediate between a trigonal bipyramid and a square pyramid. In this complex, the ligand pzol.2 is tridentated and forms two metallocycle rings. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.11.041
• 作为产物：
  描述：

  1-phenyl-3-pyridin-2-yl-propane-1,3-dione 、 2-肼基乙醇 以 乙醇 为溶剂， 反应 5.0h， 以43%的产率得到2-(3-phenyl-5-(pyridin-2-yl)-1H-pyrazol-1-yl)ethanol
  参考文献：
  名称：

  Preparation, separation and characterisation of two regioisomers of a N-hydroxyalkylpyridylpyrazole ligand: A structural investigation of their coordination to Pd(II), Pt(II) and Zn(II) centres

  摘要：

  The reaction of the beta-diketone 1-phenyl-3-(pyridyn-2-yl)propane-1,3-dione, and the monosubstituted hydrazine 2-hydroxyethylhydrazine has been investigated. Two regioisomers were identified, 2-(3-phenyl-5-(pyridyn-2-yl)-1H-pyrazol-1-yl)ethanol (pzol.1) and 2-(5-phenyl-3-(pyridyn-2-yl)-1H-pyrazol-1-yl) ethanol (pzol.2) in 57:43 ratio. The separation of the regioisomers was done by silica column chromatography using ethyl acetate as eluent.Palladium(II) and platinum(II), [MCl2(pzol.1)(2)], [MCl2(pzol.2)], and zinc(II), [ZnCl2(pzol.1)], [ZnCl2(pzol.2)] complexes were synthesised and characterised. The crystals and molecular structures of [PdCl2(pzol.2)]center dot H2O and [ZnCl2(pzol.2)] were solved by X-ray diffraction, and consist of mononuclear complexes. In complex [PdCl2(pzol.2)]center dot H2O, the Pd(II) centre has a typical square planar geometry, with a slight tetrahedral distortion. The tetra-coordinated atom is bonded to one pyridinic nitrogen, one pyrazolic nitrogen and two chlorine atoms in cis disposition. The pzol.2 ligand acts as a bidentate chelate forming a five-membered metallocycle ring. In complex [ZnCl2(pzol.2)], the Zn(II) is five-coordinated with two Zn-N bonds (Zn-N-pz and Zn-N-py), one Zn-OH bond and two Zn-Cl bonds. The coordination geometry is intermediate between a trigonal bipyramid and a square pyramid. In this complex, the ligand pzol.2 is tridentated and forms two metallocycle rings. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.11.041

文献信息

• Highly Efficient Pyridylpyrazole Ligands for the Heck Reaction. A Combined Experimental and Computational Study
  作者：Vanessa Montoya、Josefina Pons、Vicenç Branchadell、Jordi Garcia-Antón、Xavier Solans、Mercè Font-Bardía、Josep Ros

  DOI：10.1021/om7009182

  日期：2008.3.24

  Several [PdCl2(L)] complexes, where L is a pyridylpyrazole ligand, have been used as precatalysts in the Heck reactions between phenyl halides and tert-butyl acrylate. The used ligands differ from each other in the substitution at N1. The best results are obtained when this substituent is a hydroxyethyl group, and the corresponding complexes yield good results even for the reaction of chlorobenzene. Theoretical studies have shown that the presence of an OH group in the N1 substituent favors Pd-X dissociation, since it stabilizes the resulting cationic complex and the dissociation becomes thermodynamically favorable even in the absence of a coordinating solvent molecule.
• 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.