1,2-双(4-甲氧基苯基)咪唑 | 852525-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,2-双(4-甲氧基苯基)咪唑
• 英文名称: 1,2-bis(4-methoxyphenyl)-1H-imidazole
• 英文别名: 1,2-bis(4-methoxyphenyl)imidazole
• CAS: 852525-37-2
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: FYBRCHQDFZRMCM-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  467.2±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-双(4-甲氧基苯基)咪唑 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到1,2-bis(4-hydroxyphenyl)-1H-imidazole
  参考文献：
  名称：

  Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1H-Imidazoles

  摘要：

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

  DOI：

  10.1021/jm061106t
• 作为产物：
  描述：

  对茴香胺盐酸盐 在 manganese(IV) oxide 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 51.0h， 生成 1,2-双(4-甲氧基苯基)咪唑
  参考文献：
  名称：

  Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1H-Imidazoles

  摘要：

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

  DOI：

  10.1021/jm061106t

文献信息

• Palladium- and Copper-Mediated Direct C-2 Arylation of Azoles — Including Free (NH)-Imidazole, -Benzimidazole and -Indole — Under Base-Free and Ligandless Conditions
  作者：Fabio Bellina、Silvia Cauteruccio、Renzo Rossi

  DOI：10.1002/ejoc.200500957

  日期：2006.3

  thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without

  首次钯和铜介导的噻唑、恶唑、N-甲基咪唑和 N-芳基咪唑以及游离 (NH)-咪唑、-苯并咪唑和-吲哚的 C-2 芳基化，在无配体和碱-描述了免费条件。在这些前所未有的条件下实现了完全的选择性，允许使用含有碱敏感基团的底物，例如咪唑、苯并咪唑或吲哚的 NH 基团，而无需事先保护。在游离(NH)-咪唑、-苯并咪唑和-吲哚的芳基化反应中未检测到N-芳基化产物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Regioselective Synthesis of 1,5-Diaryl-1<i>H</i>-imidazoles by Palladium-Catalyzed Direct Arylation of 1-Aryl-1<i>H</i>-imidazoles
  作者：Fabio Bellina、Silvia Cauteruccio、Luisa Mannina、Renzo Rossi、Stéphane Viel

  DOI：10.1021/jo050274a

  日期：2005.5.1

  A variety of 1,5-diaryl-1H-imidazoles have been regioselectively synthesized by direct coupling of 1-aryl-1H-imidazoles with aryl iodides or bromides in DMF in the presence of CsF as the base and a catalyst precursor consisting of a mixture of Pd(OAc)2 and AsPh3. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium(II) halide species

  在CsF作为碱和由以下成分组成的催化剂前体的存在下，通过在DMF中将1-芳基-1 H-咪唑与芳基碘化物或溴化物直接偶联，已选择性地合成了多种1,5-二芳基-1 H-咪唑。 Pd（OAc）2和AsPh 3的混合物。在这项综合研究中获得的数据支持了涉及芳基钯（II）卤化物物种对咪唑环的亲电攻击的反应机理。有趣的是，已经发现在该研究中合成的一些咪唑衍生物对人肿瘤细胞系表现出显着的细胞毒性活性。
• Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides
  作者：Fabio Bellina、Chiara Calandri、Silvia Cauteruccio、Renzo Rossi

  DOI：10.1016/j.tet.2006.12.068

  日期：2007.2

  -indole, with aryl iodides under ligandless and base-free conditions provides regioselectively the required 2-arylheterocycle derivatives in high yields. 2-Aryl-1-phenyl-1H-imidazoles can also be prepared by a one-pot domino HALEX and Pd- and Cu-mediated arylation reactions of 1-phenyl-1H-imidazole with activated and unactivated aryl bromides under base-free and ligandless conditions. The protocol

  在无配体和无碱条件下，各种π电子足够的杂芳烃（包括游离的（NH）-咪唑，-苯并咪唑和-吲哚）与Pd和Cu介导的反应与芳基碘化物在区域上选择性地提供了所需的2-高产率的芳基杂环衍生物。2-芳基-1-苯基-1 H-咪唑也可以通过在碱性条件下通过一锅多米诺骨牌HALEX以及Pd和Cu介导的1-苯基-1 H-咪唑与活化和未活化的芳基溴化物的芳基化反应来制备自由和无配体的条件。已经发现涉及使用芳基碘化物的2-芳基唑的合成方案适用于有效制备三种生物活性化合物和乙酰肝素酶抑制剂合成中的关键中间体。
• Regiocontrolled Synthesis of 1,2-Diaryl-1H-imidazoles by Palladium- and Copper-Mediated Direct Coupling of 1-Aryl-1H-imidazoles with Aryl Halides under Ligandless Conditions
  作者：Fabio Bellina、Silvia Cauteruccio、Luisa Mannina、Renzo Rossi、Stéphane Viel

  DOI：10.1002/ejoc.200500636

  日期：2006.2

  involving the formation of an organocopper(I) derivatives followed by a transmetallation reaction with an arylpalladium(II) halide species and a reductive elimination, is proposed. New one-step procedures for the synthesis of 1,2,5-triaryl-1H-imidazoles, based on palladium- and copper-mediated arylation of 1-aryl-1H-imidazoles, have also been developed. Interestingly, some imidazole derivatives prepared in

  通过在 DMF 中将 1-芳基-1H-咪唑与芳基碘化物或溴化物直接偶联，以中等至高产率区域选择性地合成了多种 1,2-二芳基-1H-咪唑，包括选择性 COX-2 抑制剂。在无配体条件下存在 CsF 和催化量的 Pd(OAc)2。提出了这种新的高区域选择性 C-2 芳基化反应的可能机制，包括形成有机铜 (I) 衍生物，然后与芳基钯 (II) 卤化物物种进行金属转移反应和还原消除。还开发了基于钯和铜介导的 1-芳基-1H-咪唑芳基化的新一步法合成 1,2,5-三芳基-1H-咪唑。有趣的是，已发现本研究中制备的某些咪唑衍生物对某些人类肿瘤细胞系具有显着的细胞毒活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Oxidative annulations via double CH bond cleavages: Approach to quinoline derivatives
  作者：Zhenghui Liu、Shien Guo、Peng Wang、Zhenzhong Yan、Tiancheng Mu

  DOI：10.1002/aoc.6156

  日期：2021.4

  system via oxidative annulations was proposed. A systematic exploration was completed. All kinds of reaction parameters were determined. And 55 kinds of target molecules were obtained with moderate to high yields. Combination of double oxidants made the conversion proceed smoothly. A clear reaction mechanism was put forward. Adjacent π systems might provide assistance for realizing the activation of relatively

  提出了一种通过铑催化氧化铑催化复杂的喹啉衍生物的方法。系统的探索完成了。确定了各种反应参数。并以中等至高收率获得了55种目标分子。双重氧化剂的结合使转化顺利进行。提出了明确的反应机理。相邻的π系统可能通过形成五元金属环中间体而为实现相对不活泼的咪唑环的C（5）H的活化提供帮助。此外，放大实验验证了实际的适用性。