1-(4-chlorophenyl)-3-(4-methoxyphenyl)-5-phenyl-1H-pyrazole | 1432596-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-3-(4-methoxyphenyl)-5-phenyl-1H-pyrazole
• 英文别名: 1-(4-chlorophenyl)-3-(4-methoxyphenyl)-5-phenylpyrazole；1-(4-Chlorophenyl)-3-(4-methoxyphenyl)-5-phenylpyrazole
• CAS: 1432596-27-4
• 化学式: C₂₂H₁₇ClN₂O
• 分子量: 360.843
• InChiKey: UIGCDPWNUNZXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二硫代苯甲酸甲酯 在 potassium tert-butylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.0h， 生成 1-(4-chlorophenyl)-3-(4-methoxyphenyl)-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity

  摘要：

  Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2-propenones (prepared in situ by base-induced alkylation of 1,3-monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in. refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.

  DOI：

  10.1021/jo400599e

文献信息

• Pyrazoles and<i>C</i>-Imidoylaziridines through [4+1] Annulation and [2+1] Cycloaddition of 1-Azabuta-1,3-dienes with a Synthetic Equivalent of Phthalimidonitrene
  作者：Aleksandr Stukalov、Viktor V. Sokolov、Vitalii V. Suslonov、Mikhail A. Kuznetsov

  DOI：10.1002/ejoc.201700172

  日期：2017.5.10

  [4+1] annulation. This transformation is supposed to proceed by nitrenoid attack onto a lone pair of electrons of the imine nitrogen atom to give the vinylazomethine imine, followed by its 1,5-electrocyclization into pyrazoline and further aromatization into pyrazole. Rare examples of 2-imidoyl-1-phthalimidoaziridines that are formed by competitive [2+1] cycloaddition onto the C=C bond were isolated

  N-氨基邻苯二甲酰亚胺与 1,2,4-triaryl-1-azabuta-1,3-diene 的氧化加成，在大多数情况下，导致 1,3,5-三芳基吡唑以中等至良好的产率通过 [4 +1] 年化。这种转化应该是通过类氮烯攻击亚胺氮原子的一对孤对电子来进行的，得到乙烯基偶氮甲碱亚胺，然后将其 1,5-电环化成吡唑啉并进一步芳构化成吡唑。对于在亚胺氮原子上具有缺电子芳基取代基的 1-氮杂二烯，通过在 C=C 键上的竞争性 [2+1] 环加成形成的 2-imidoyl-1-phthalimidoaziridines 的罕见例子以低产率分离。