1-Benzyloxy-2-methylsulfanyl-1H-imidazole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Benzyloxy-2-methylsulfanyl-1H-imidazole
• 英文别名: 1-(benzyloxy)-2-(methylthio)-1H-imidazole；2-methylsulfanyl-1-phenylmethoxyimidazole
• 化学式: C₁₁H₁₂N₂OS
• 分子量: 220.295
• InChiKey: GGEWGSSAABOVCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  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-2-methylsulfanyl-1H-imidazole
  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+

文献信息

• HAUSER, H.;KLOTZER, W.;KRUG, V.;RZEHAK, J.;SANDRIESER, A.;SINGEWALD, N., SCI. PHARM., 56,(1988) N, C. 235-241
  作者：HAUSER, H.、KLOTZER, W.、KRUG, V.、RZEHAK, J.、SANDRIESER, A.、SINGEWALD, N.

  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.

表征谱图