1-Benzyloxy-2-(tert-butyl-dimethyl-silanyl)-1H-imidazole | 202211-97-0

• 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
• 英文名称: 1-Benzyloxy-2-(tert-butyl-dimethyl-silanyl)-1H-imidazole
• 英文别名: Tert-butyl-dimethyl-(1-phenylmethoxyimidazol-2-yl)silane
• CAS: 202211-97-0
• 化学式: C₁₆H₂₄N₂OSi
• 分子量: 288.465
• InChiKey: XOJPJYABBYAKNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyloxy-2-(tert-butyl-dimethyl-silanyl)-1H-imidazole 在 正丁基锂 作用下， -78.0~20.0 ℃ 、133.32 Pa 条件下， 反应 0.08h， 生成 1-Benzyloxy-2-trimethylsilanyl-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+
• 作为产物：
  描述：

  1-(苄氧基)-1H-咪唑 、 叔丁基二甲基氯硅烷 在 正丁基锂 作用下， 生成 1-Benzyloxy-2-(tert-butyl-dimethyl-silanyl)-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

• 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