1-苄氧基咪唑3-氧化物 | 1027036-69-6

• 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-苄氧基咪唑3-氧化物
• 英文名称: 1-benzyloxyimidazole-3-oxide
• 英文别名: 1-Oxido-3-phenylmethoxyimidazol-1-ium
• CAS: 1027036-69-6
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: CAKLLGFFJVPNJV-UHFFFAOYSA-N

物化性质

• 沸点：
  359.6±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄氧基咪唑3-氧化物 在 正丁基锂 、 三氯化磷 作用下， 以 氯仿 为溶剂， 反应 1.58h， 生成 1-Benzyloxy-1H-imidazole-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation

  摘要：

  Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

  DOI：

  10.1021/jo970355+
• 作为产物：
  描述：

  溴甲苯 、 1-hydroxyimidazole-3-oxide 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到1-苄氧基咪唑3-氧化物
  参考文献：
  名称：

  非对称 1,3-二（烷氧基）咪唑鎓盐的合成和晶体结构

  摘要：

  摘要 通过1-羟基咪唑-3-氧化物的逐步烷基化合成了一系列非对称的1,3-二(烷氧基)咪唑鎓盐。随后通过在 2 位溴化使季盐官能化。示例性地制备了2-叠氮基咪唑鎓盐和咪唑啉-2-硫酮。两个 2-溴-1-烷氧基-3-甲基氧基咪唑鎓三溴化物和汞 (II)-硫酮配合物的晶体结构已通过 X 射线衍射确定。

  DOI：

  10.1515/znb-2017-0089

文献信息

• Laus, Gerhard; Schwaerzler, Alexander; Bentivoglio, Gino, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2008, vol. 63, # 4, p. 447 - 464
  作者：Laus, Gerhard、Schwaerzler, Alexander、Bentivoglio, Gino、Hummel, Michael、Kahlenberg, Volker、Wurst, Klaus、Kristeva, Elka、Schuetz, Johannes、Kopacka, Holger、Kreutz, Christoph、Bonn, Guenther、Andriyko, Yuriy、Nauer, Gerhard、Schottenberger, Herwig

  DOI：——

  日期：——
• Pinto, Luis F. V.; Justino, Goncalo C.; Vieira, Abel J. S. C., ARKIVOC, 2010, vol. 2010, # 5, p. 17 - 23
  作者：Pinto, Luis F. V.、Justino, Goncalo C.、Vieira, Abel J. S. C.、Prabhakar, Sundaresan、Lobo, Ana M.

  DOI：——

  日期：——
• Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation
  作者：Birgitte Langer Eriksen、Per Vedsø、Sandrine Morel、Mikael Begtrup

  DOI：10.1021/jo970355+

  日期：1998.1.1

  Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.
• Synthesis and crystal structures of non-symmetric 1,3-di(alkyloxy)imidazolium salts
  作者：Markus Jochriem、Christian G. Kirchler、Gerhard Laus、Klaus Wurst、Holger Kopacka、Thomas Müller、Herwig Schottenberger

  DOI：10.1515/znb-2017-0089

  日期：2017.8.28

  Abstract A series of non-symmetric 1,3-di(alkyloxy)imidazolium salts were synthesized by stepwise alkylation of 1-hydroxyimidazole-3-oxide. The quaternary salts were subsequently functionalized by bromination in 2-position. A 2-azidoimidazolium salt and an imidazoline-2-thione were prepared exemplarily. Crystal structures of two 2-bromo-1-alkyloxy-3-methyloxyimidazolium tribromides and a mercury(II)-thione

  摘要 通过1-羟基咪唑-3-氧化物的逐步烷基化合成了一系列非对称的1,3-二(烷氧基)咪唑鎓盐。随后通过在 2 位溴化使季盐官能化。示例性地制备了2-叠氮基咪唑鎓盐和咪唑啉-2-硫酮。两个 2-溴-1-烷氧基-3-甲基氧基咪唑鎓三溴化物和汞 (II)-硫酮配合物的晶体结构已通过 X 射线衍射确定。