5-Bromo-2-(tert-butyl-dimethyl-silanyl)-1-methyl-1H-imidazole | 191734-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Bromo-2-(tert-butyl-dimethyl-silanyl)-1-methyl-1H-imidazole
• 英文别名: (5-bromo-1-methylimidazol-2-yl)-tert-butyl-dimethylsilane
• CAS: 191734-24-4
• 化学式: C₁₀H₁₉BrN₂Si
• 分子量: 275.264
• InChiKey: RIYSDQBNZGPJLU-UHFFFAOYSA-N

物化性质

• 沸点：
  290.9±32.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-(tert-butyl-dimethyl-silanyl)-1-methyl-1H-imidazole 在 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.33h， 生成 2-tert-butyldimethylsilyl-5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methyl-1H-imidazole
  参考文献：
  名称：

  Homonuclear Diels–Alder dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to synthesis of 12,12′-dimethylageliferin

  摘要：

  Homonuclear Diels-Alder dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, which is the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.027
• 作为产物：
  描述：

  2-(叔丁基二甲基甲硅烷基)-1-甲基-1H-咪唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 5-Bromo-2-(tert-butyl-dimethyl-silanyl)-1-methyl-1H-imidazole
  参考文献：
  名称：

  Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00230-8

文献信息

• Synthesis of 2,5-dilithio-1-methylimidazole
  作者：Gideon Shapiro、Martin Marzi

  DOI：10.1016/s0040-4039(00)79166-0

  日期：1993.5

  C5 to C2 position migrations of 2-trialkylsilyl and thiophenyl groups have been observed upon lithiation at the C5-position of corresponding C2-substituted 1-methylimidazoles. Double bromine-lithium exchange of 1-methyl-2,5-dibromoimidazole (5) affords a facile, quantitative and unequivocal synthesis of 2,5-dilithio-1-mediyl-imidazole (4). Reaction of 4 with one equivalent of DMF occurs selectively at the C5 position to give 1-methyl ole-5-carboxaldehyde (1).