4-methyl-1-phenylimidazole | 150587-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-1-phenylimidazole
• 英文别名: 4-methyl-1-phenyl-1H-imidazole
• CAS: 150587-21-6
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: TZFGLMGQQDEFMH-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C(Solv: chloroform (67-66-3))
• 沸点：
  294.6±9.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-1-phenylimidazole 在 potassium phosphate 、 正丁基锂 、 methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 生成 3-(5-(4-methyl-1-phenyl-1H-imidazol-2-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione
  参考文献：
  名称：

  WO2024054832A1

  摘要：

  公开号：
• 作为产物：
  描述：

  1-苯基-4-甲基吡唑 以 乙腈 为溶剂， 生成 4-methyl-1-phenylimidazole
  参考文献：
  名称：

  Phototransposition chemistry of 1-phenylpyrazole. Experimental and computational studies

  摘要：

  Photophysical and photochemical properties of 1-phenylpyrazole and 3-,4-, and 5-methyl-1-phenylpyrazoles have been investigated. INDO/S calculations agree with experimental measurements which show that the S1 and T1 states of these compounds are pi,pi* in character. Upon S0 --> S1(pi,pi*) excitation, these 1-phenylpyrazoles undergo phototransposition via a P4 permutation pathway. This process is consistent with a mechanism involving initial N-N bond cleavage followed by a 1,2-shift and cyclization to form the 1-phenylimidazole product. The 1,2-shift may occur via an undetected azirine intermediate. Whereas the regioselectivity of the reaction may be due to the stability of the N-phenyl radical, the quantum efficiencies of reaction and fluorescence are remarkably dependent on the location of the methyl group in the pyrazole ring. AM1 calculations provide energy-minimized structures for the more reactive 1-phenylpyrazole and 4-methyl- and 5-methyl-1-phenylpyrazoles in which the phenyl and pyrazole rings are perpendicular as required to stabilize the transition state for N-N bond cleavage. In contrast, such a perpendicular energy minimized S1 structure could not be obtained for the least reactive S1(pi,pi*) 3-methyl-1-phenylpyrazole which undergoes mainly radiative return to the ground state.

  DOI：

  10.1021/ja00070a008

文献信息

• Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading
  作者：Zhe Wu、Zhi-Qin Wang、Hua Cheng、Zhong-Hui Zheng、Ye Yuan、Cheng Chen、Francis Verpoort

  DOI：10.1016/j.apcata.2021.118443

  日期：2022.1

  Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1]

  醇和水/氢氧化物的无受体脱氢偶联 (ADC) 是一种新兴且优雅的生产羧酸的方法。因此，迫切需要为这种有吸引力的转化开发活性和实用的催化剂/催化体系。在此，我们通过[Ru-1] 的配体调谐设计并制造了一系列环金属化N-杂环卡宾-Ru (NHC-Ru) 配合物，我们之前工作中的高级复合体。令人欣慰的是，在露天环境中，以超低的 Ru 负载量（62.5 ppm）有效地实现了羧酸的克级合成。此外，对不同的辅助 NHC 配体和其他参数对该催化过程的影响进行了深入研究，同时进行了进一步的系统研究，为[Ru-1] - [Ru-7]的活性趋势提供了理论依据。最后，定量绿色指标的确定表明，目前的工作表现出优于代表性文献报告的优势。希望这项研究可以为从事金属催化 ADC 反应的研究人员提供有价值的输入。
• α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles
  作者：Chunling Yuan、Yingdai Zhao、Li Zheng

  DOI：10.1055/s-0039-1690226

  日期：2019.12

  The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C–N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

  这里报告了α-D-半乳糖醛酸水合物（GalA）作为潜在的O-供体配体的首次应用。N-杂环化合物与芳基卤化物或芳基硼酸的C-N偶联可以轻松进行，并且具有良好的官能团容忍性和选择性特征。这些N-芳基唑允许快速获得几种药用中间体，并且也可以轻松转化为各种其他有趣的骨架。
• Unique copper–salen complex: an efficient catalyst for N-arylations of anilines and imidazoles at room temperature
  作者：Ankur Gogoi、Gayatri Sarmah、Anindita Dewan、Utpal Bora

  DOI：10.1016/j.tetlet.2013.10.084

  日期：2014.1

  activity of a unique Cu–salen type complex in N-arylation of anilines with arylboronic acids in water. The protocol is found to be applicable for a wide range of electronically diversified arylboronic acids and anilines with excellent yields of the isolated product. Further the scope of this protocol has been extended to the synthesis of various N-aryl imidazoles in iso-propanol.

  我们在这里报告了一种独特的Cu-salen型配合物在水中苯胺与芳基硼酸的N-芳基化反应中的催化活性。已发现该方案适用于多种电子多样化的芳基硼酸和苯胺，且分离出的产物收率极高。此外，该方案的范围已扩展到在异丙醇中合成各种N-芳基咪唑。
• [EN] SULFONYLAMINOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS SULFONYLAMINOPYRIDINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016001341A1

  公开（公告）日：2016-01-07

  Provided are sulfonylaminopyridine compounds that are inhibitors of ITK kinase, compositions containing these compounds and methods for treating diseases mediated by ITK kinase. In particular, provided are compounds of Formula (I), (II) or (III), stereoisomers, tautomers, solvates, prodrugs or pharmaceutically acceptable salts thereof, where n, R1, R2, R3, R6 and R7 are defined herein, pharmaceutical compositions comprising the compound and a pharmaceutically acceptable carrier, adjuvant or vehicle, methods of using the compound or composition in therapy, for example, for treating a disease or condition mediated by ITK kinase in a patient.

  提供了一种磺酰氨基吡啶化合物，它们是ITK激酶的抑制剂，包含这些化合物的组合物以及治疗由ITK激酶介导的疾病的方法。具体来说，提供了Formula (I)、(II)或(III)的化合物，立体异构体、互变异构体、溶剂合物、前药或其药用可接受的盐，其中n、R1、R2、R3、R6和R7在此处定义，包括含有该化合物和药用可接受的载体、辅料或载体的药物组合物，使用该化合物或组合物进行治疗的方法，例如，用于治疗患有由ITK激酶介导的疾病或病况的患者。
• Copper−Diamine-Catalyzed <i>N</i>-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles
  作者：Jon C. Antilla、Jeremy M. Baskin、Timothy E. Barder、Stephen L. Buchwald

  DOI：10.1021/jo049658b

  日期：2004.8.1

  This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as

  本文详细介绍了铜催化的π-过量氮杂环的N-芳基化反应。芳基碘化物或芳基溴化物与常见的氮杂环（吡咯，吡唑，吲唑，咪唑和三唑）的偶联成功地用衍生自二胺配体和CuI的催化剂进行了高收率的偶联。发现一般条件可耐受芳基卤化物或杂环上的官能团，例如醛，酮，醇，伯胺和腈。使用本文报道的条件，受阻的芳基卤化物或杂环也被发现是合适的底物。