吡啶,2-[1-辛基-5-(三氟甲基)-1H-吡唑-3-基]- | 192711-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 吡啶,2-[1-辛基-5-(三氟甲基)-1H-吡唑-3-基]-
• 英文名称: 2-(1-octyl-5-trifluoromethyl-1H-pyrazol-3-yl)-pyridine
• 英文别名: 1-Octyl-3-(2-pyridinyl)-5-(trifluoromethyl)-1H-pyrazole；2-[1-octyl-5-(trifluoromethyl)pyrazol-3-yl]pyridine
• CAS: 192711-32-3
• 化学式: C₁₇H₂₂F₃N₃
• 分子量: 325.377
• InChiKey: VSTBZYLUMMLIRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-(5-(三氟甲基)-1H-吡唑-3-基)吡啶	3-trifluoromethyl-5-(2-pyridyl)pyrazole	3974-71-8	C9H6F3N3	213.162

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 吡啶,2-[1-辛基-5-(三氟甲基)-1H-吡唑-3-基]- 以 乙腈 为溶剂， 以63%的产率得到dichloropalladium(II)(2-(1-octyl-5-trifluoromethyl-1H-pyrazol-3-yl)pyridine)
  参考文献：
  名称：

  Pd(II) complexes containing N-alkyl-3-pyridine-5-trifluoromethyl pyrazole ligands: Synthesis, NMR studies and X-ray crystal structures

  摘要：

  Palladium [PdCl2(L)] complexes with N-alkylpyridylpyrazole derived ligands [2-(5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L-1), 2(1-ethyl-5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L-2), 2-(1-octyl-5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L), and 2-(3-pyridin2-yl-5-trifluoromethyl-pyrazol-1-yl)ethanol (L-4) were synthesised. The crystal and molecular structures of [PdCl2,(L)] (L = L-2, L-3, L-4) were resolved by X-ray diffraction, and consist of monomeric cis-[PdC](2)(L)] molecules. The palladium centre has a typical square-planar geometry, with a slight tetrahedral distortion. The tetra-coordinate metal atom is bonded to one pyridinic nitrogen, one pyrazolic nitrogen and two chlorine ligands in cis disposition. Reaction of L (L-2, L-4) with [Pd(CH3CN)(4)](BF4)(2), in the ratio 1M:2L, gave complexes [Pd(L)](2)(BF4)(2). Treatment of [PdCl2(L)] (L = L-2, L-4) with NaBF4 and pyridine (py) and treatment of the same complexes with AgBF4 and triphenylphosphine (PPh3) Yielded [Pd(L)(py)(2)](BF4)(2) and [Pd(L)(PPh3)(2)](BF4)(2) complexes, respectively. Finally, reaction of [PdCl2(L)] with 1 equiv of AgBF4 yields [PdCI(L-4)](BF4). (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2006.08.058
• 作为产物：
  描述：

  4,4,4-三氟-1-(2-吡啶)丁烷-1,3-二酮 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 吡啶,2-[1-辛基-5-(三氟甲基)-1H-吡唑-3-基]-
  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

• 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.
• 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.
• Pd(II) complexes containing N-alkyl-3-pyridine-5-trifluoromethyl pyrazole ligands: Synthesis, NMR studies and X-ray crystal structures
  作者：Vanessa Montoya、Josefina Pons、Jordi Garcia-Antón、Xavier Solans、Mercè Font-Bardia、Josep Ros

  DOI：10.1016/j.ica.2006.08.058

  日期：2007.2

  Palladium [PdCl2(L)] complexes with N-alkylpyridylpyrazole derived ligands [2-(5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L-1), 2(1-ethyl-5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L-2), 2-(1-octyl-5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (L), and 2-(3-pyridin2-yl-5-trifluoromethyl-pyrazol-1-yl)ethanol (L-4) were synthesised. The crystal and molecular structures of [PdCl2,(L)] (L = L-2, L-3, L-4) were resolved by X-ray diffraction, and consist of monomeric cis-[PdC](2)(L)] molecules. The palladium centre has a typical square-planar geometry, with a slight tetrahedral distortion. The tetra-coordinate metal atom is bonded to one pyridinic nitrogen, one pyrazolic nitrogen and two chlorine ligands in cis disposition. Reaction of L (L-2, L-4) with [Pd(CH3CN)(4)](BF4)(2), in the ratio 1M:2L, gave complexes [Pd(L)](2)(BF4)(2). Treatment of [PdCl2(L)] (L = L-2, L-4) with NaBF4 and pyridine (py) and treatment of the same complexes with AgBF4 and triphenylphosphine (PPh3) Yielded [Pd(L)(py)(2)](BF4)(2) and [Pd(L)(PPh3)(2)](BF4)(2) complexes, respectively. Finally, reaction of [PdCl2(L)] with 1 equiv of AgBF4 yields [PdCI(L-4)](BF4). (c) 2006 Elsevier B.V. All rights reserved.