2-methyl-1-phenylimidazole | 150587-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-1-phenylimidazole
• 英文别名: N-(phenyl)-5-methylimidazole；5-methyl-1-phenyl-1H-imidazole；5-Methyl-1-phenylimidazole
• CAS: 150587-22-7
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: WTWDYIRAELZONQ-UHFFFAOYSA-N

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：

  2-methyl-1-phenylimidazole 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-iodo-5-methyl-1-phenyl-1H-imidazole
  参考文献：
  名称：

  Aryl-4-ethynyl-isoxazole derivatives

  摘要：

  本发明涉及式I的芳基-4-乙炔-异恶唑衍生物，其中R1至R5如规范中所述，并且其药用盐。这类化合物具有高亲和力和选择性结合到GABA A α5受体结合位点，可用作认知增强剂或用于治疗阿尔茨海默病等认知障碍。

  公开号：

  US20070287739A1
• 作为产物：
  描述：

  5-甲基-1-苯基-1H-吡唑 以 乙腈 为溶剂， 生成 2-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

• PAR4 AGONIST PEPTIDES
  申请人：Bristol-Myers Squibb Company

  公开号：US20130289238A1

  公开（公告）日：2013-10-31

  The present invention provides PAR4 agonist peptides. These peptides are useful for developing robust PAR4 receptor assays.

  本发明提供PAR4激动肽。这些肽对于开发强大的PAR4受体测定方法非常有用。
• 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。
• Copper(I)–USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type <i>O</i>-, <i>N</i>-, <i>S</i>-, and <i>C</i>-Arylation Reactions: Scope and Application to Total Synthesis
  作者：Tony Garnier、Mathieu Danel、Valentin Magné、Anthony Pujol、Valérie Bénéteau、Patrick Pale、Stefan Chassaing

  DOI：10.1021/acs.joc.8b00620

  日期：2018.6.15

  copper(I)-doped zeolite CuI–USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C–O bond

  掺杂铜（I）的沸石Cu I- USY被证明是用于各种Ullmann型偶联反应的通用，高效且可回收的催化剂。这种催化材料易于制备且价格便宜，可在无配体的条件下实现多种O-，N-，S-和C-亲核试剂的芳基化和杂芳基化，同时具有大的官能团相容性。这种催化剂促进C-O键形成的功能在3-甲基obovatol（一种具有生物学相关性的天然存在的二芳基醚）的全合成中得到了进一步证明。从机理的角度出发，已经提出了两种竞争途径，这取决于亲核试剂的性质并与所获得的结果一致。
• Simple Copper Salt-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides
  作者：Liangbo Zhu、Peng Guo、Gaocan Li、Jingbo Lan、Rugang Xie、Jingsong You

  DOI：10.1021/jo0712289

  日期：2007.10.1

  Relatively mild and highly efficient CuI-catalyzed N-arylation procedures for nitrogen-containing heterocycles (e.g., imidazoles, benzimidazoles, pyrroles, pyrazoles, indoles, triazoles, etc.) with aryl and heteroaryl halides have been developed. The protocols can be performed easily and tolerate a number of functional groups, such as ester, nitrile, nitro, ketone, free hydroxyl, and free primary amine

  已经开发了相对温和且高效的CuI催化的含氮杂环（例如咪唑，苯并咪唑，吡咯，吡唑，吲哚，三唑等）与芳基和杂芳基卤化物的N芳基化方法。该方案可以容易地进行并且耐受芳基卤化物上的许多官能团，例如酯，腈，硝基，酮，游离羟基和游离伯胺。
• An efficient copper-catalyzed coupling of aryl halides with imidazoles
  作者：Ayumu Kiyomori、Jean-François Marcoux、Stephen L. Buchwald

  DOI：10.1016/s0040-4039(99)00291-9

  日期：1999.4

  Copper-catalyzed N-arylation of imidazoles can be accomplished using (CuOTf)2·benzene as a copper source and Cs2CO3 as a base in xylenes at 110–125 °C. Addition of 1,10-phenanthroline (phen) and trans,trans-dibenzylideneacetone (dba) was crucial to the success of the process. The products, N-arylimidazoles, were isolated in high yields.

  铜催化的咪唑的N-芳基化反应可以使用（CuOTf）2 ·苯作为铜源，而Cs 2 CO 3作为二甲苯中的碱在110–125°C下完成。添加1,10-菲咯啉（phen）和反式，反式-二苄基丙酮（dba）对于该方法的成功至关重要。以高收率分离出产物N-芳基咪唑。