1-benzoyl-3,5-dimethyl-1H-pyrazole | 1137-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyl-3,5-dimethyl-1H-pyrazole
• 英文别名: (3,5‐dimethyl‐1H‐pyrazol‐1‐yl)(phenyl)methanone；(3,5-dimethyl-1H-pyrazol-1-yl)(phenyl)methanone；(3,5-dimethyl-pyrazol-1-yl)-phenyl-methanone；(3,5-dimethylpyrazol-1-yl)phenylmethanone；N-benzoyl-3,5-dimethyl-pyrazole；1-benzoyl-3,5-dimethylpyrazole；(3,5-Dimethylpyrazol-1-yl)-phenylmethanone
• CAS: 1137-11-7
• 化学式: C₁₂H₁₂N₂O
• mdl: MFCD00686515
• 分子量: 200.24
• InChiKey: AHNLSPFBSUPXHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  231-234 °C
• 沸点：
  349.4±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-3,5-dimethyl-1H-pyrazole 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 苯甲醛
  参考文献：
  名称：

  Ried; Koenigstein, Justus Liebigs Annalen der Chemie, 1959, vol. 622, p. 37,40

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基吡唑 在 乙醚 、 ethyl magnesium halide 作用下， 生成 1-benzoyl-3,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  Mingoia; Ingraffia, Gazzetta Chimica Italiana, 1934, vol. 64, p. 279,282

  摘要：

  DOI：

文献信息

• Cu_1.5 PMo₁₂ O₄₀ -catalyzed condensation cyclization for the synthesis of substituted pyrazoles
  作者：Guo-Ping Yang、Xing He、Bing Yu、Chang-Wen Hu

  DOI：10.1002/aoc.4532

  日期：2018.11

  A convenient and direct approach has been developed for the preparation of pyrazole derivatives by the condensation cyclization of hydrazines/hydrazide and 1,3‐diketones in the presence of Cu1.5PMo12O40 (0.33 mol%) under mild conditions (r.t.‐60 °C, 10–30 min). Notably, the reaction was found to be scalable as 99% yield was obtained when the reaction was performed at a 5‐mmol scale. This solvent‐free

  在温和的条件下（rt-60），在Cu 1.5 PMo 12 O 40（0.33 mol％）存在下，通过肼/酰肼和1,3-二酮的缩合环化反应，已经开发了一种方便直接的方法来制备吡唑衍生物。°C，10–30分钟）。值得注意的是，当反应在5 mmol规模下进行时，发现该反应可扩展，产率为99％。这种无溶剂和无卤素的催化体系代表了吡唑的一种有效的经济和环保方法。
• Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
  作者：Alexandra A. Sysoeva、Alexander S. Novikov、Mikhail V. Il'in、Vitalii V. Suslonov、Dmitrii S. Bolotin

  DOI：10.1039/d1ob01158h

  日期：——

  electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2 > 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive

  本报告展示了静电表面电位分布分析在评估一系列基于唑鎓的卤素键供体的相对催化活性方面的成功应用。观察到卤素原子上 σ 空穴的正静电势与模型反应活化的吉布斯自由能（即，卤素抽象和羰基活化）。实验证实了所应用方法的预测能力。还确定了基于唑鎓的卤素键供体的催化活性通常由唑鎓循环的结构决定，而杂环上的取代基对活性的影响有限。最终，这项研究强调了四种最有希望的唑鎓卤素键供体，预计它们将表现出高催化活性。
• Sulfamic Acid (H₂NSO₃H): A Low-Cost, Mild, and Efficient Catalyst for the Synthesis of Substituted N-Phenylpyrazoles Under Solvent-Free Conditions
  作者：Mohan R. Shetty、Shriniwas D. Samant

  DOI：10.1080/00397911.2010.540365

  日期：2012.5.15

  Abstract N-Phenylpyrazoles are synthesized by condensing phenylhydrazine and 1,3-diketones in the presence of a catalytic amount of sulfamic acid, a mild and an efficient solid acid catalyst, under solvent-free conditions. This condensation proceeds smoothly in shorter reaction time. GRAPHICAL ABSTRACT

  摘要 N-苯基吡唑是通过苯肼和1,3-二酮在催化量的氨基磺酸（一种温和高效的固体酸催化剂）存在下在无溶剂条件下缩合合成的。该缩合在较短的反应时间内顺利进行。图形概要
• The Preparation of<i>N</i>-Acylpyrazoles and Their Behavior Toward Alcohols
  作者：Choji Kashima、Hajime Harada、Isanobu Kita、Iwao Fukuchi、Akira Hosomi

  DOI：10.1055/s-1994-25406

  日期：——

  According to four different methods, various types of N-acylpyrazoles were prepared from the corresponding pyrazoles and carboxylic acids or their acid chlorides. Although N-acylpyrazoles were inert to alcohols under neutral or weakly basic conditions, the alcoholysis was dramatically accelerated by the action of strong acid or base. On the basis of these chemical properties, the regioselective synthesis of methyl benzyl 2,2-dimethylglutarate was achieved by selective protection and functionalization of a carboxylic acid derivative using N-acylpyrazoles.

  根据四种不同的方法，从相应的吡唑和羧酸或其酰氯制备了多种类型的N-酰基吡唑。尽管在中性或弱碱性条件下，N-酰基吡唑对醇呈惰性，但强酸或碱的作用下，醇解反应显著加速。基于这些化学性质，通过选择性保护和功能化羧酸衍生物，成功实现了甲基苄基2,2-二甲基戊二酸酯的区域选择性合成。
• Iodonium salts as efficient iodine(<scp>iii</scp>)-based noncovalent organocatalysts for Knorr-type reactions
  作者：Sevilya N. Yunusova、Alexander S. Novikov、Natalia S. Soldatova、Mikhail A. Vovk、Dmitrii S. Bolotin

  DOI：10.1039/d0ra09640g

  日期：——

  Hypervalent iodine(III)-derivatives display higher catalytic activity than other aliphatic and aromatic iodine(I)– or bromine(I)-containing substrates for a Knorr-type reaction of N-acetyl hydrazides with acetyl acetone to give N-acyl pyrazoles. The highest activity was observed for dibenziodolium triflate, for which 10 mol% resulted in the generation of N-acyl pyrazole from acyl hydrazide and acetyl

  对于N-乙酰酰肼与乙酰丙酮的克诺尔型反应生成N-酰基吡唑，高价碘 ( III ) 衍生物比其他脂肪族和芳香族含碘 () 或溴 () 的底物表现出更高的催化活性。三氟甲磺酸二苯并碘鎓的活性最高，10 mol% 会导致酰肼和乙酰丙酮在 50 °C 下反应 3.5-6 小时，生成N-酰基吡唑，分离收率高达 99%。 1 H NMR滴定数据和DFT计算表明碘( III )的催化活性是由与酮的结合引起的。