2-(1-octyl-5-phenyl-1H-pyrazol-3-yl)-pyridine | 192711-31-2

• 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-(1-octyl-5-phenyl-1H-pyrazol-3-yl)-pyridine
• 英文别名: 2-(1-octyl-5-phenyl-1H-pyrazol-3-yl)pyridine；2-(1-Octyl-5-phenylpyrazol-3-yl)pyridine
• CAS: 192711-31-2
• 化学式: C₂₂H₂₇N₃
• 分子量: 333.476
• InChiKey: KRFLVZUOQXUSJH-UHFFFAOYSA-N

物化性质

• 沸点：
  480.1±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-octyl-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-octyl-5-phenyl-1H-pyrazol-3-yl)pyridine)(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-octyl-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

• PROCESS FOR EPOXIDATION OF ARYL ALLYL ETHERS
  申请人：Dow Global Technologies Inc.

  公开号：EP1080084B1

  公开（公告）日：2004-05-06
• Molybdenum-Catalyzed Olefin Epoxidation: Ligand Effects
  作者：Werner R. Thiel、Jörg Eppinger

  DOI：10.1002/chem.19970030508

  日期：1997.5

  AbstractWe synthesized substituted pyrazolylpyridine ligands to examine their donor properties by spectroscopic (IR, NMR) and computational (AM 1) methods. The influence of the substitution patterns on spectroscopic and thermodynamic features of molybdenum oxobisperoxo complexes [(L–L)MoO(O2)2] (L–L=2‐(1‐alkyl‐3‐pyrazolyl)pyridine/pyrazine) correlates with the activities of the complexes in catalytic olefin epoxidation reactions. This further proof for the relation between the Lewis acidity and the catalytic activity of epoxidation catalysts supports a reaction mechanism in which the peroxo complex activates the oxidizing agent (H2O2, ROOH) instead of directly transferring an oxygen atom from a π2‐peroxo ligand to the olefin.
• 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.
• US6087513A
  申请人：——

  公开号：US6087513A

  公开（公告）日：2000-07-11
• [EN] EPOXIDATION PROCESS FOR ARYL ALLYL ETHERS<br/>[FR] PROCEDE D'EPOXYDATION D'ARYL-ALLYL ETHERS
  申请人：——

  公开号：WO1999062894A2

  公开（公告）日：1999-12-09

  [EN] A process for making an aromatic glycidyl ether epoxy compound by contacting an allyl ether made from the hydroxy moiety of a hydroxy-containing aromatic compound with an inorganic or organic hydroperoxide oxidant in the presence of a transition metal complex catalyst, wherein at least (a) the allyl ether is conformationally restricted or (b) the transition metal complex catalyst contains at least one or more stable ligands attached to the transition metal. The process of the present invention provides for epoxidizing aryl allyl ethers with high epoxidation yield (for example, greater than 70 percent to 90 percent) and high hydroperoxide selectivity (for example, greater than 70 percent to 90 percent).
  [FR] La présente invention concerne un procédé permettant la réalisation d'un composé époxy de glycidyl-éther aromatique. En l'occurrence, on prend un allyl-éther issu du groupe fonctionnel hydroxy d'un composé aromatique comportant un hydroxy et on le met en contact avec comme oxydant un hydroperoxyde organique ou inorganique en présence d'un catalyseur à base de métal de transition. Il faut néanmoins (a) que l'allyl-éther emporte des restrictions de conformation ou (b) que le catalyseur à base de métal de tansition contienne au moins un ou plusieurs ligands stables se rattachant au métal de transition. Le procédé de l'invention permet ainsi une époxydation d'aryl-allyl éthers avec un haut degré d'époxydation (typiquement plus de 70 % à 90 %) et une haute sélectivité de l'hydroperoxyde (typiquement plus de 70 % à 90 %).