5-(4-methoxyphenyl)-1-methyl-3-phenyl-1H-pyrazole | 66870-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methoxyphenyl)-1-methyl-3-phenyl-1H-pyrazole
• 英文别名: 1-methyl-3-phenyl-5-(4-methoxyphenyl)pyrazole；1-methyl-3-phenyl-5-p-methoxyphenylpyrazole；5-(4-methoxy-phenyl)-1-methyl-3-phenyl-1H-pyrazole；5-p-Anisyl-1-methyl-3-phenylpyrazol；5-(4-Methoxyphenyl)-1-methyl-3-phenylpyrazole
• CAS: 66870-45-9
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: VQRSQLRQVBBSFR-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C(Solv: hexane (110-54-3))
• 沸点：
  420.9±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基查耳酮 在 氧气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 5-(4-methoxyphenyl)-1-methyl-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  Heterocycles: 2—Regiospecific addition of methylhydrazine to acetylenic ketones

  摘要：

  AbstractThe reaction of 1‐p‐methoxyphenyl‐3‐phenyl‐2‐propen‐1‐one and 3‐p‐methoxyphenyl‐1‐phenyl‐2‐propen‐1‐one with methylhydrazine gave 1‐methyl‐3‐p‐methoxyphenyl‐5‐phenylpyrazoline and 1‐methyl‐3‐phenyl‐5‐p‐methoxyphenylpyrazoline, respectively. These compounds, on oxidation, gave 1‐methyl‐3‐p‐methoxyphenyl‐5‐phenylpyrazole(2) and 1‐methyl‐3‐phenyl‐5‐p‐methoxyphenylpyrazole, respectively. When methyl‐hydrazine was made to react with 1‐p‐methoxyphenyl‐3‐phenyl‐2‐propyn‐1‐one, a pyrazole was obtained which proved to be identical with 2. Confirmatory evidence for this identity was obtained from their spectral data.

  DOI：

  10.1002/omr.1270210404

文献信息

• Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles from <i>N</i>-Alkylated Tosylhydrazones and Terminal Alkynes
  作者：Yuanfang Kong、Meng Tang、Yun Wang

  DOI：10.1021/ol403447g

  日期：2014.1.17

  An efficient synthesis of 1,3,5-trisubstituted pyrazoles from N-alkylated tosylhydrazones and terminal alkynes was developed. The protocol was applied to a wide range of substrates and demonstrated excellent tolerance to a variety of substituents, including both electron-donating and -withdrawing groups. In comparison with the common approaches for substituted pyrazole syntheses, this methodology proceeded

  开发了由N-烷基化的甲苯磺酰terminal和末端炔烃有效合成1,3,5-三取代的吡唑的方法。该规程适用于多种底物，并表现出对各种取代基（包括供电子基团和吸电子基团）的出色耐受性。与用于取代的吡唑合成的常规方法相比，该方法以完全的区域选择性进行，特别是在R 2和R 3是相似的取代基的情况下。
• One-Pot Coupling–Coupling–Cyclocondensation Synthesis of Fluorescent Pyrazoles
  作者：Alissa C. Götzinger、Florian A. Theßeling、Corinna Hoppe、Thomas J. J. Müller

  DOI：10.1021/acs.joc.6b01326

  日期：2016.11.4

  ondensation syntheses of pyrazoles and pyrimidines were developed by taking advantage of the provisional, sequentially Pd-catalyzed one-pot generation of alkynones from aryl iodides, ethynylmagnesium bromide, and acid chlorides. This one-pot methodology allows the concise, diversity-oriented generation of a set of donor-, acceptor-, and donor–acceptor-substituted pyrazoles, which are interesting fluorophores

  吡唑和嘧啶的连续四组分偶联-偶联-环缩合反应是利用芳基碘化物，乙炔基溴化镁和酰氯的临时，顺序钯催化的一锅法生成的，从而开发了吡唑和嘧啶。这种一锅法方法可以简洁，面向多样性地生成一组供体，受体和供体受体取代的吡唑，这是有趣的荧光团。最明显的是，供体-受体吡唑显示出明显的红移发射最大值，并具有明显的正溶剂变色性，整个范围从363 nm（环己烷）到595 nm（乙腈）。DFT和TD-DFT计算可阐明电子结构和光物理行为。在光子激发下，明显的电荷转移特性变得明显，
• Aluminum Chloride Mediated Reactions of N-Alkylated Tosyl­hydrazones and Terminal Alkynes: A Regioselective Approach to 1,3,5-Trisubstituted Pyrazoles
  作者：Meng Tang、Yun Wang、Hu Wang、Yuanfang Kong

  DOI：10.1055/s-0035-1561646

  日期：——

  Abstract Aluminum chloride mediated reactions of N-alkylated tosylhydrazones and terminal alkynes are reported. The protocol is applied to a wide range of substrates, and demonstrates excellent functional group tolerance. A series of 1,3,5-trisubstituted pyrazoles is prepared in good to high yields with complete regioselectivity. Aluminum chloride mediated reactions of N-alkylated tosylhydrazones and

  摘要 报道了氯化铝介导的N-烷基化甲苯磺酰and与末端炔烃的反应。该协议适用于广泛的底物，并证明了出色的官能团耐受性。制备了一系列1,3,5-三取代的吡唑类，具有良好的收率，具有很高的区域选择性。 报道了氯化铝介导的N-烷基化甲苯磺酰and与末端炔烃的反应。该协议适用于广泛的底物，并证明了出色的官能团耐受性。制备了一系列1,3,5-三取代的吡唑类，具有良好的收率，具有很高的区域选择性。
• The Preparation of Substituted Pyrazoles from β,β-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process
  作者：Richard Taylor、Sandra Beltrán-Rodil、Michael Edwards、David. Pugh、Mark Reid

  DOI：10.1055/s-0029-1218521

  日期：2010.3

  consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from α-hydroxyketones. The first, a tandem MnO 2 -mediated oxidation/Ramirez olefination reaction, provides a facile route to β,β-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura

  描述了从 α-羟基酮区域选择性两步合成 1,3,5-三取代吡唑的两个连续串联过程。第一个是串联 MnO 2 介导的氧化/拉米雷斯烯化反应，为 β,β-二溴烯酮提供了一条简便的途径。然后，这些有价值的 1,3-二羰基合成子可以通过第二个串联肼缩合/Suzuki-Miyaura 交叉偶联反应转化为 1,3,5-三取代的吡唑。使用这些程序，一系列芳基和烷基 α-羟基酮已被区域选择性地转化为 1,3,5-三取代的吡唑。
• Bishop, Brian C.; Brands, Karel M. J.; Gibb, Andrew D., Synthesis, 2004, # 1, p. 43 - 52
  作者：Bishop, Brian C.、Brands, Karel M. J.、Gibb, Andrew D.、Kennedy, Derek J.

  DOI：——

  日期：——