1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole | 1088567-34-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole
• 英文别名: 1-(3,5-di(trifluoromethyl)phenyl)imidazole；1-(3,5-Bis(trifluoromethyl)phenyl)-1H-imidazole；1-[3,5-bis(trifluoromethyl)phenyl]imidazole
• CAS: 1088567-34-3
• 化学式: C₁₁H₆F₆N₂
• 分子量: 280.172
• InChiKey: UKVCJMKHZDYEDP-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  267.1±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole 在 六氟磷酸钾 作用下， 以 水 为溶剂， 反应 48.0h， 生成 1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrimidine-2-yl)imidazolium hexafluorophosphate
  参考文献：
  名称：

  贫电子半不稳定的阳离子型NHC钯复合物-合成，结构和催化活性†

  摘要：

  我们提出了一种新型的带有两个卡宾配体的新型钯NHC复合物，它们带有不同的芳基取代基和一个半不稳定的嘧啶基。它们可以由咪唑鎓盐通过银的金属转移途径合成为不含卤化物的钯（II）前体或通过乙酸钯直接去质子化。对于四个配合物，我们可以通过X射线衍射实验确定其固态结构。NMR光谱学和DFT计算获得的见解表明，在溶液中，两种潜在的双齿配体在螯合和非螯合配位模式之间互换。这些配位模式的偏好取决于不同配体的空间影响。该配合物被证明是炔烃加氢芳基化的活性催化剂，其性能通过DFT计算得到合理化。

  DOI：

  10.1039/c8dt03373k
• 作为产物：
  描述：

  咪唑 、 3,5-双三氟甲基溴苯 在 copper(l) iodide 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以81%的产率得到1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis and characterization of 1,3-diamino-graphene as a heterogeneous ligand for a CuI-catalyzed C–N coupling reaction

  摘要：

  1,3-二氨基石墨烯被合成并用作CuI催化的C-N偶联反应的高效异质配体。

  DOI：

  10.1039/c5nj02625c

文献信息

• Salts Comprising Aryl-Alkyl-Substituted Imidazolium and Triazolium Cations and the Use Thereof
  申请人：Strassner Thomas

  公开号：US20110105761A1

  公开（公告）日：2011-05-05

  The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts according to the invention as solvents, solvent additives, or extraction means, and to the use of the salts according to the invention, for example as solvents or solvent additives in chemical reactions, as extracting agents for the separation of substances, or for storing hydrogen. According to the invention, the object is achieved by salts of the general formula (I), where X— is an anion, Y1 and Y2 are CH, or Y1 is CH and Y2 is N, or Y1 is N and Y2 is CH, n is a number from 1 up to an including 18, Q is selected from —CH3, —OH, —ORx, —S03H, —S03Rx, —COOH, —COORx, —CORx, NH2, —NHRx, —N(Rx)2, and —CH(Rx)2, Z is H or Rx, R1, R2, R3, R4 and R5 independently from each other are —H, -halogen, —N02, —NH2, —NHRx, —N(Rx)2, —Rx, —COORx or —ORx, where Rx is an optionally substituted and/or branched C1 to C18-alkyl group, excluding compounds of the general formula (I), where Y1 and Y2 are CH and R1, R2, R3, R4 and R5 are H, excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1=R3=R5=CH3 is true, n=1, 2, 6 and Q=CH3 is true, excluding compounds of the general formula (I), where Y1 is CH and Y2 is N, R1, R2, R3, R4 and R5 are H, n=1 is true, and Q=CH3 is true, and excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1, R2, R4, R5=H is true, R3=ORx is true, and Rx is a hydrocarbon having 3 or 12 carbon atoms.

  本发明涉及包含新颖芳基-烷基取代咪唑和三唑阳离子以及任意阴离子的盐。该发明还涉及一种化学转化和物质分离的方法，包括作为溶剂、溶剂添加剂或萃取剂的本发明盐，并且涉及使用本发明的盐，例如作为化学反应中的溶剂或溶剂添加剂，作为物质分离的萃取剂，或用于储存氢。根据本发明，通过一般式(I)的盐实现了该目的，其中X—是一个阴离子，Y1和Y2为CH，或者Y1为CH且Y2为N，或者Y1为N且Y2为CH，n是从1到18的数字，Q从—CH3、—OH、—ORx、—S03H、—S03Rx、—COOH、—COORx、—CORx、NH2、—NHRx、—N(Rx)2和—CH(Rx)2中选择，Z为H或Rx，R1、R2、R3、R4和R5彼此独立地为—H、-卤素、—N02、—NH2、—NHRx、—N(Rx)2、—Rx、—COORx或—ORx，其中Rx是一个可选择地取代和/或支链的C1到C18烷基基团，不包括一般式(I)的化合物，其中Y1和Y2为CH且R1、R2、R3、R4和R5为H，不包括一般式(I)的化合物，其中Y1和Y2为CH，R1=R3=R5=CH3为真，n=1、2、6且Q=CH3为真，不包括一般式(I)的化合物，其中Y1为CH且Y2为N，R1、R2、R3、R4和R5为H，n=1为真，且Q=CH3为真，不包括一般式(I)的化合物，其中Y1和Y2为CH，R1、R2、R4、R5=H为真，R3=ORx为真，且Rx是一个具有3或12个碳原子的碳氢化合物。
• Simple and Convenient Methods for N-Arylation of Heterocycles and Diphenylamine
  作者：Mariappan Periasamy、Laxhmaiah Alakonda

  DOI：10.1055/s-0031-1290162

  日期：2012.4

  Abstract N-Arylation of NH-heterocycles and diphenylamine with various aryl halides, using a readily accessible ligand-free potassium tert-butoxide/iron(III) oxide/dimethyl sulfoxide reagent system, gives the corresponding N-aryl derivatives in 47–97% yields. N-Arylation of NH-heterocycles and diphenylamine with various aryl halides, using a readily accessible ligand-free potassium tert-butoxide/iron(III)

  摘要 使用易于获得的无配体叔丁醇钾/三氧化二铁/二甲亚砜试剂体系，将NH-杂环和二苯胺与各种芳基卤化物进行N-芳基化反应，得到相应的N-芳基衍生物，产率为47-97％ 。 使用易于获得的无配体叔丁醇钾/三氧化二铁/二甲亚砜试剂体系，将NH-杂环和二苯胺与各种芳基卤化物进行N-芳基化反应，得到相应的N-芳基衍生物，产率为47-97％ 。
• Facile CuI-Catalyzed Arylation of Azoles and Amides Using Simple Enaminones as Efficient Ligands
  作者：Cuirong Sun、Cungui Cheng、Gonglei Sun、Jieping Wan

  DOI：10.1055/s-0029-1217958

  日期：2009.10

  found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 °C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.

  (E)-3-(二甲氨基)-1-(2-羟基苯基)prop-2-en-1-one 被发现是铜催化的唑类和酰胺与芳基卤化物在温和条件下 N-芳基化的极好配体. 该反应在具有广泛官能团兼容性的 MeCN 中于 82°C 下进行。配体和CuI的组合被证明是促进芳基卤化物与唑类和酰胺偶联反应的有效催化体系。
• A Versatile and Efficient Cu-Catalyzed N-Arylation of Aromatic Cyclic Secondary Amines with Aryl Halides
  作者：Haitao Yang、Zhiwei Miao、Ruyu Chen

  DOI：10.2174/157017811795684974

  日期：2011.6.1

  A copper-catalyzed coupling reaction of aryl halides with various aromatic cyclic secondary amines in DMSO has been developed efficiently. The versatile and efficient copper catalyst system is of wide-spread and practical application in cross-coupling reactions.

  已经有效地开发了一种在DMSO中将芳基卤化物与各种芳香环状次级胺进行铜催化偶联反应的方法。这种多功能且高效的铜催化剂体系在交叉偶联反应中具有广泛和实用的应用。
• Salts comprising aryl-alkyl-substituted imidazolium and triazolium cations and the use thereof
  申请人：Strassner Thomas

  公开号：US09260397B2

  公开（公告）日：2016-02-16

  The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts according to the invention as solvents, solvent additives, or extraction means, and to the use of the salts according to the invention, for example as solvents or solvent additives in chemical reactions, as extracting agents for the separation of substances, or for storing hydrogen. According to the invention, the object is achieved by salts of the general formula (I), where X— is an anion, Y1 and Y2 are CH, or Y1 is CH and Y2 is N, or Y1 is N and Y2 is CH, n is a number from 1 up to an including 18, Q is selected from —CH3, —OH, —ORx, —S03H, —S03Rx, —COOH, —COORx, —CORx, NH2, —NHRx, —N(Rx)2, and —CH(Rx)2, Z is H or Rx, R1, R2, R3, R4 and R5 independently from each other are —H, -halogen, —N02, —NH2, —NHRx, —N(Rx)2, —Rx, —COORx or —ORx, where Rx is an optionally substituted and/or branched C1 to C18-alkyl group, excluding compounds of the general formula (I), where Y1 and Y2 are CH and R1, R2, R3, R4 and R5 are H, excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1=R3=R5=CH3 is true, n=1, 2, 6 and Q=CH3 is true, excluding compounds of the general formula (I), where Y1 is CH and Y2 is N, R1, R2, R3, R4 and R5 are H, n=1 is true, and Q=CH3 is true, and excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1, R2, R4, R5=H is true, R3=ORx is true, and Rx is a hydrocarbon having 3 or 12 carbon atoms.

  本发明涉及含有新型芳基-烷基取代咪唑和三唑阳离子以及任意阴离子的盐。本发明还涉及使用本发明的盐作为溶剂、溶剂添加剂或萃取剂的化学转化和物质分离方法，以及使用本发明的盐，例如作为化学反应中的溶剂或溶剂添加剂，作为分离物质的萃取剂，或用于储存氢。根据本发明，目标是通过公式（I）的盐来实现，其中X-是阴离子，Y1和Y2是CH，或者Y1是CH而Y2是N，或者Y1是N而Y2是CH，n是从1到18的数字，Q从-CH3，-OH，-ORx，-S03H，-S03Rx，-COOH，-COORx，-CORx，NH2，-NHRx，-N（Rx）2，和-CH（Rx）2中选择，Z是H或Rx，R1，R2，R3，R4和R5互相独立地是-H，-卤素，-N02，-NH2，-NHRx，-N（Rx）2，-Rx，-COORx或-ORx，其中Rx是一个可选的和/或支链的C1到C18烷基，不包括公式（I）中Y1和Y2都是CH，而R1，R2，R3，R4和R5都是H的化合物，不包括公式（I）中Y1和Y2都是CH，而R1 = R3 = R5 = CH3为真，n = 1、2、6和Q = CH3为真的化合物，不包括公式（I）中Y1是CH而Y2是N，而R1，R2，R3，R4和R5都是H，n = 1为真，Q = CH3为真的化合物，以及不包括公式（I）中Y1和Y2都是CH，而R1，R2，R4，R5 = H为真，R3 = ORx为真，而Rx是具有3或12个碳原子的碳氢化合物的化合物。