三甲基-(1-甲基咪唑-2-基)硅烷 | 35342-89-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 三甲基-(1-甲基咪唑-2-基)硅烷
• 英文名称: 1-methyl-2-(trimethylsilyl)-1H-imidazole
• 英文别名: (1-methylimidazol-2-yl)trimethylsilane；1-methyl-2-trimethylsilylimidazole；N-trimethylsilylimidazole；1-methyl-2-TMS-imidazole；1-methyl-2-trimethylsilanyl-1H-imidazole；Trimethyl(1-methyl-2-imidazolyl)silan；1H-Imidazole, 1-methyl-2-(trimethylsilyl)-；trimethyl-(1-methylimidazol-2-yl)silane
• CAS: 35342-89-3
• 化学式: C₇H₁₄N₂Si
• 分子量: 154.287
• InChiKey: UAYUBMFLEZJDIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  三甲基-(1-甲基咪唑-2-基)硅烷 在 三氯化磷 作用下， 以66%的产率得到2-[二(1-甲基-1H-咪唑-2-基)膦基]-1-甲基-1H-咪唑
  参考文献：
  名称：

  Synthesis and coordinating properties of heterocyclic-substituted tertiary phosphines

  摘要：

  DOI：

  10.1021/jo00347a023
• 作为产物：
  描述：

  N-甲基咪唑 、 三甲基氯硅烷 在 正丁基锂 作用下， 生成 三甲基-(1-甲基咪唑-2-基)硅烷
  参考文献：
  名称：

  Bakhtiar, Cuross; Smith, Edward H., Journal of the Chemical Society. Perkin transactions I, 1994, # 3, p. 239 - 244

  摘要：

  DOI：

文献信息

• N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit
  作者：Anatolii P. Marchenko、Heorgii N. Koidan、Anastasiya N. Huryeva、Evgeniy V. Zarudnitskii、Aleksandr A. Yurchenko、Aleksandr N. Kostyuk

  DOI：10.1021/jo101177h

  日期：2010.11.5

  It has been experimentally proven that the reaction of 1- or 1,2-disubstituted imidazoles with diorganylphosphorus(III) halides proceeds via initial formation of N-phosporylated imidazolium salts. Treatment of these salts with strong bases results in phosphorylation of the parent imidazoles at the 2- or 5-positions, correspondingly. In a previous case, imidazol-2-ylidenes are formed as intermediates

  实验已经证明1-或1，2-二取代的咪唑与二有机基磷（III）卤化物的反应是通过最初形成N-磷酸化的咪唑鎓盐而进行的。用强碱处理这些盐会相应地导致母体咪唑在2或5位发生磷酸化。在先前的情况下，形成咪唑-2-亚基作为中间体。在N1和N3原子上都带有空间要求或/和π供体基团的情况下，将1,3-二取代的咪唑鎓盐与NaN（SiMe 3）2进行去质子化反应可得到新的稳定的N-磷取代的Arduengo型卡宾。
• Gold(i) complexes of water-soluble diphos-type ligands: Synthesis, anticancer activity, apoptosis and thioredoxin reductase inhibition
  作者：Corinna Wetzel、Peter. C. Kunz、Matthias U. Kassack、Alexandra Hamacher、Philip Böhler、Wim Watjen、Ingo Ott、Riccardo Rubbiani、Bernhard Spingler

  DOI：10.1039/c1dt10368g

  日期：——

  Gold(I) complexes of imidazole and thiazole-based diphos type ligands were prepared and their potential as chemotherapeutics investigated. Depending on the ligands employed and the reaction conditions complexes [L(AuCl)2] and [L2Au]X (X = Cl, PF6) are obtained. The ligands used are diphosphanes with azoyl substituents R2P(CH2)2PR2 R = 1-methylimidazol-2-yl (1), 1-methylbenzimidazol-2-yl (4), thiazol-2-yl (5) and benzthiazol-2-yl (6)} as well as the novel ligands RPhP(CH2)2PRPh R = 1-methylimidazol-2-yl (3)} and R2P(CH2)3PR2 R = 1-methylimidazol-2-yl (2)}. The cytotoxic activity of the complexes was assessed against three human cancer cell lines and a rat hepatoma cell line and correlated to the lipophilicity of the compounds. The tetrahedral gold complexes [(3)2Au]PF6 and [(5)2Au]PF6 with intermediate lipophilicity (logD7.4 = 0.21 and 0.25) showed significant cytotoxic activity in different cell lines. Both compounds induce apoptosis and inhibit the enzymes thioredoxin reductase and glutathione reductase.

  研究人员制备了咪唑和噻唑二磷配体的金（I）配合物，并对其作为化疗药物的潜力进行了研究。根据所用配体和反应条件的不同，可以得到[L(AuCl)2]和[L2Au]X（X = Cl，PF6）配合物。使用的配体是带有偶氮取代基 R2P(CH2)2PR2 R = 1-甲基咪唑-2-基（1），1-甲基苯并咪唑-2-基（4）、噻唑-2-基 (5) 和苯并噻唑-2-基 (6)} 以及新型配体 RPhP( )2PRPh R = 1-甲基咪唑-2-基 (3)} 和 R2P( )3PR2 R = 1-甲基咪唑-2-基 (2)}。评估了这些配合物对三种人类癌细胞系和一种大鼠肝癌细胞系的细胞毒性活性，并将其与化合物的亲脂性联系起来。具有中等亲油性（logD7.4 = 0.21 和 0.25）的四面体金配合物 [(3)2Au]PF6 和 [(5)2Au]PF6 在不同细胞系中显示出显著的细胞毒性活性。这两种化合物都能诱导细胞凋亡并抑制硫代氧化还原酶和谷胱甘肽还原酶。
• Novel multitopic diphos-type ligands.
  作者：Peter C. Kunz、Corinna Wetzel、Melanie Bongartz、Anna Louisa Noffke、Bernhard Spingler

  DOI：10.1016/j.jorganchem.2010.04.028

  日期：2010.7

  Seven novel imidazole and thiazole derivatives of diphos-type ligands are presented. They are of the general structure R(2)P(CH(2))(2)PR(2), where R is imidazol-2-yl (1), 1-methylimidazol-2-yl (2), 1-methyl-benzimidazol-2-yl (3), 1-methylimidazol-5-yl (4), 2-isopropylimidazol-4(5)-yl (5), thiazol-2-yl (6), benzothiazol-2-yl (7), thiazol-4-yl (8) or thiazol-5-yl (9). Syntheses involved direct metallation or halogen-metal exchange reactions. Their solubility, especially in aqueous solution, is strongly dependent on the nature of the substituents as is their partition coefficient log D. The crystal structures of compounds 2, 3, 7a and 9 as well as the structure of the rhodium complex [(2)(2)Rh(2)Cl(2)]Cl(2) (10) have been determined. (C) 2010 Elsevier B. V. All rights reserved.
• Investigation of carbon-2 substituted imidazoles and their corresponding ionic liquids
  作者：Chen Liao、Xiang Zhu、Xiao-Guang Sun、Sheng Dai

  DOI：10.1016/j.tetlet.2011.08.010

  日期：2011.10

  The functionality at the C-2 position of the imidazole ring plays a key role in defining the chemical properties of the imidazoles and their corresponding ionic liquids. Imidazoles 1-6 with different C-2 functionality were synthesized and their corresponding ionic liquids were systematically investigated. Based on their physical properties the six imidazoles can be divided into three groups. (1) The imidazoles 2 and 3 are capable of self-polymerization to form poly(ionic liquid)s, and they are characterized with a strong leaving group at the C-2 position. (2) The imidazoles 4 and 5 can form ionic liquids, but they are very sensitive to moisture. (3) The imidazoles 1 and 6 can form stable ionic liquids, and their stabilities were influenced by the electronic effects of the substituents at the C-2 position. Published by Elsevier Ltd.
• Hydrolyses of 2-(trimethylsilyl) N1-heterocycles. Involvement of zwitterions in the hydrolysis of 2-(trimethylsilyl)-N-methylimidazole, 2-(trimethylsilyl)pyridine, and 2-[(trimethylsilyl)methyl]-N-methylimidazole
  作者：R. S. Brown、H. Slebocka-Tilk、J. M. Buschek、J. G. Ulan

  DOI：10.1021/ja00332a038

  日期：1984.10