2-methyl-1-(thiophen-2-yl)-1H-imidazole

• 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-(thiophen-2-yl)-1H-imidazole
• 英文别名: 2-methyl-1-thiophen-2-yl-1H-imidazole；2-Methyl-1-thiophen-2-ylimidazole
• 化学式: C₈H₈N₂S
• 分子量: 164.231
• InChiKey: DKDCMRXOXSGKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1-(thiophen-2-yl)-1H-imidazole 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以79%的产率得到8-methyl-4,5-diphenylimidazo[1,5-a]thieno[3,2-e]pyridine
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Direct Selective C(5)–H Oxidative Annulations of 2-Substituted Imidazoles and Alkynes by Double C–H Activation

  摘要：

  Double C-H activations of C(5)-H and Csp(2)-H of 2-substituted N-vinyl- or arylimidazoles were realized without heteroatom-directing assistance by rhodium(III) catalyst. A subsequent oxidative annulation reaction with alkynes efficiently produced aza-fused heterocycles with high molecular complexity in low to excellent yields.

  DOI：

  10.1021/ol400537b
• 作为产物：
  描述：

  2-溴噻吩 、 2-甲基咪唑 在 copper(II) acetate monohydrate 、 caesium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 以40%的产率得到2-methyl-1-(thiophen-2-yl)-1H-imidazole
  参考文献：
  名称：

  Ligand-free copper-catalysed coupling reaction of heteroaryl bromides with imidazole and benzimidazole

  摘要：

  据报道，在相对温和的条件下，以稳定易得的醋酸铜（II）为催化剂，以碳酸铯为碱，通过将杂芳基溴化物与咪唑或苯并咪唑偶联合成 N-杂芳基咪唑，可获得中等至良好收率的产品。

  DOI：

  10.3184/030823409x12506792542864

文献信息

• Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles
  作者：Ryan A. Altman、Erica D. Koval、Stephen L. Buchwald

  DOI：10.1021/jo070807a

  日期：2007.8.1

  10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good

  发现4,7-二甲氧基-1,10-菲咯啉（L1c）是在温和条件下铜催化的咪唑和苯并咪唑与芳基碘化物和溴化物的N-芳基化反应的有效配体。系统的进一步优化表明，聚乙二醇的加入会加速该反应。各种受阻和功能化的咪唑，苯并咪唑和芳基卤化物均以良好的转化率达到了极好的收率。杂芳基卤化物也以中等至良好的产率偶联。我们还介绍了从一系列偶联反应中获得的结果，这些反应直接比较了L1c与其他最近报道的配体的使用。
• An Efficient N-Arylation of Heterocycles with Aryl-, Heteroaryl-, and Vinylboronic Acids Catalyzed by Copper Fluorapatite
  作者：Mannepalli Lakshmi Kantam、Gopaladasu Tirupati Venkanna、Kota Balaji Shiva Kumar、Vura Bala Subrahmanyam

  DOI：10.1002/hlca.200900326

  日期：2010.5

  N‐Arylation of N‐containing heterocycles, such as pyrazoles, imidazoles, and benzimidazoles with aryl‐, heteroaryl‐, and vinylboronic acids was efficiently carried out by copper fluorapatite (CuFAP) catalyst in MeOH at room temperature under base‐free conditions. The N‐arylated heterocycles were isolated in good‐to‐excellent yields.

  Ñ含N杂环，如吡唑，咪唑，并用苯并咪唑的-Arylation芳基- ，杂芳基- ，和vinylboronic酸被有效通过铜氟磷灰石（CuFAP）催化剂在MeOH在室温下游离碱条件下进行的。的N-芳基化的杂环在良好至优异的产率进行分离。
• BICYCLE THIOPHENES AND THIAZOLES
  申请人：——

  公开号：US20020025974A1

  公开（公告）日：2002-02-28

  Certain imidazo benzthiophenes/thiazoles of the formula: 1 where Z is N or C-Y (Y is absent where the imidazole containing substituent is attached at the 3-position); n is 0 or 1; Y is independently selected from the group consisting of hydrogen, C 1-4 alkyl, bromine, chlorine, iodide, trifluoromethyl, C 1-4 alkoxy, —SO 2 NH 2 and nitro; X is independently selected from the group consisting of hydrogen, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl and phenyl; and A is independently selected from the group consisting of hydrogen, C 1-4 alkyl, chlorine, trifluoromethyl, C 1-4 alkoxy and nitro, or is absent where the imidazole containing substituent is attached at the 2-position; are &agr; 2 -adrenoceptor modulators which are useful in the treatment of hypertension, glaucoma, sexual dysfunction, depression, attention deficit hyperactivity disorder, the need for anesthesia, cardiac arrythmia or the need for analgesia.

  某些咪唑苯并噻吩/噻唑的化学式为 1 其中 Z 是 N 或 C-Y（如果含咪唑的取代基连接在 3 位，则不含 Y）； n 为 0 或 1； Y 独立地选自氢、C 1-4 烷基、溴、氯、碘、三氟甲基、C 1-4 烷氧基、-SO 2 NH 2 和硝基； X 独立地选自氢、羟基、C 1-4 烷基、C 1-4 烷氧基、三氟甲基和苯基组成的组；以及 A 独立地选自氢、C 1-4 烷基、C 1-4 烷氧基、三氟甲基和苯基组成的组 1-4 烷基、氯、三氟甲基、C 1-4 烷氧基和硝基组成的组中，或者在含咪唑的取代基连接在 2 位时不存在； 是&agr； 2 -肾上腺素受体调节剂，可用于治疗高血压、青光眼、性功能障碍、抑郁症、注意缺陷多动障碍、麻醉需要、心律失常或镇痛需要。
• CuI catalyzed C–N bond forming reactions between aryl/heteroaryl bromides and imidazoles in [Bmim]BF4
  作者：Xin Lv、Zhiming Wang、Weiliang Bao

  DOI：10.1016/j.tet.2006.03.026

  日期：2006.5

  By using CuI as the catalyst and L-Proline as the ligand, the Ullmann-type coupling reactions of aryl/heteroaryl bromides and imidazoles in [Bmim]BF4 at 105-115 degrees C gave the corresponding N-arylimidazoles/N-heteroarylimidazoles in good yields. The system offers a convenient, recyclable, and environmentally benign method for these coupling reactions. (c) 2006 Elsevier Ltd. All rights reserved.
• US6426356B1
  申请人：——

  公开号：US6426356B1

  公开（公告）日：2002-07-30