1-(1-咪唑)乙酸乙酯 | 10464-67-2

• 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-(1-咪唑)乙酸乙酯
• 英文名称: 1-(imidazol-1-yl)ethyl acetate
• 英文别名: 1-(1H-imidazol-1-yl)ethyl acetate；1-imidazol-1-ylethyl acetate
• CAS: 10464-67-2
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: YTTRAVMWCVFCDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1-(1-咪唑)乙酸乙酯 以 水 为溶剂， 以52%的产率得到1-乙烯基咪唑
  参考文献：
  名称：

  Synthesis of N-vinylazoles from vinyl acetate without using mercury catalysts

  摘要：

  N-Vinyl-substituted pyrazole, 3(5)-methylpyrazole, imidazole, and 1,2,4-triazole were synthesized by addition of the corresponding azoles to vinyl acetate under conditions of phase-transfer catalysis, followed by pyrolysis of N-(1-acetoxyethyl)azoles thus formed at 350-400 degrees C in the presence of water.

  DOI：

  10.1134/s1070363207120158
• 作为产物：
  描述：

  1-乙酰基咪唑 、 乙醛 在 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以40%的产率得到1-(1-咪唑)乙酸乙酯
  参考文献：
  名称：

  1-咪唑基甲基酯的简单两步合成

  摘要：

  描述了一种新的1-咪唑基甲基酯的合成方法，该合成方法是从适当的羧酸通过咪唑化物中间体开始的。

  DOI：

  10.1002/jhet.5570270362

文献信息

• Potassium Phosphate Promoted Aza-Markovnikov Addition of N-Heterocycles to Vinyl Esters
  作者：Run-tao Li、Ze-mei Ge、Song-wen Lin、Qi Sun、Tie-ming Cheng

  DOI：10.1055/s-2007-983733

  日期：2007.7

  Anhydrous potassium phosphate promoted the aza-Markovnikov addition of a variety of N-heterocycles to vinyl esters in DMF at room temperature in moderate to excellent yields.

  无水磷酸钾促进了多种含氮杂环在室温下于二甲基甲酰胺（DMF）中对乙烯基酯的马尔科夫尼科夫型加成反应，产率从中等到优秀不等。
• Solvent-free aza-Markovnikov and aza-Michael additions promoted by a catalytic amount of imidazolide basic ionic liquids
  作者：Xuewei Chen、Xuehui Li、Hongbing Song、Yu Qian、Furong Wang

  DOI：10.1016/j.tetlet.2011.04.117

  日期：2011.7

  A family of imidazolide ionic liquids were synthesized and characterized. These ionic liquids combined the virtues of strong basicity and relatively good thermal stability. Catalytic properties of these imidazolide ionic liquids were investigated and satisfactory yield was achieved when 2.0 mol % of [Bmim]Im was used as catalyst for aza-Markovnikov addition under solvent-free condition at room temperature

  合成并表征了咪唑类离子液体家族。这些离子液体结合了强碱性和相对良好的热稳定性的优点。研究了这些咪唑化物离子液体的催化性能，当在室温下在无溶剂条件下，于一小时内将2.0 mol％的[Bmim] Im用作aza-Markovnikov加成催化剂时，获得了令人满意的产率。实验结果表明，[Bmim] Im /咪唑与乙烯基酯之间不形成氢键，并且[Bmim] Im催化的氮杂-马尔可夫尼可夫加成反应也不是必须存在的。提出了[Bmim] Im催化aza-Markovnikov加成反应的可能机理。还研究了咪唑化物离子液体在氮杂-迈克尔加成中的使用。
• Basic Ionic Liquid as Catalysis and Reaction Medium:  A Novel and Green Protocol for the Markovnikov Addition of <i>N</i>-Heterocycles to Vinyl Esters, Using a Task-Specific Ionic Liquid, [bmIm]OH
  作者：Jian-Ming Xu、Bo-Kai Liu、Wei-Bo Wu、Chao Qian、Qi Wu、Xian-Fu Lin

  DOI：10.1021/jo0600914

  日期：2006.5.1

  A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide ([bmIm]OH), has been introduced as a catalyst and reaction medium for the Markovnikov addition of N-heterocycles to vinyl esters under mild conditions. The evidence for the role of this basic ionic liquid [bmIm]OH in promoting the Markovnikov addition has been given. On the basis of the evidence, a mechanism was postulated.

  已经引入碱性离子液体，即1-甲基-3-丁基咪唑鎓氢氧化物（[bmIm] OH）作为催化剂和反应介质，用于在温和条件下将N-杂环马氏化学加成到乙烯基酯上。已经给出了这种碱性离子液体[bmIm] OH在促进马尔可夫尼科夫加入中的作用的证据。根据证据，提出了一种机制。
• A novel and highly efficient protocol for Markovnikov’s addition using ionic liquid as catalytic green solvent
  作者：Jian-Ming Xu、Wei-Bo Wu、Chao Qian、Bo-Kai Liu、Xian-Fu Lin

  DOI：10.1016/j.tetlet.2006.01.001

  日期：2006.3

  A novel and highly efficient protocol for Markovnikov’s addition using ionic liquid as a catalytic green solvent is described. The strategy is especially useful in the synthesis of N-heterocycle derivatives with biological activity. This reaction widens largely the applicability of ionic liquid in organic synthesis.

  描述了使用离子液体作为催化绿色溶剂进行马尔可夫尼可夫添加的一种新颖且高效的方案。该策略在具有生物活性的N-杂环衍生物的合成中特别有用。该反应大大拓宽了离子液体在有机合成中的适用性。
• Markovnikov addition of vinyl acetate with azoles catalyzed by potassium tert-butoxide
  作者：Mazaahir Kidwai、Neeraj Kumar Mishra、Anwar Jahan

  DOI：10.1016/j.cclet.2010.10.048

  日期：2011.4

  A simple and efficient methodology for Markovnikov addition of azoles with vinyl acetate catalyzed by potassium tert-butoxide is described. N-heterocyclic compounds are synthesized from simple and commercially available starting materials under mild conditions in high yields.

  描述了一种简单有效的方法，用于叔丁醇钾催化马尔可夫尼可夫与乙酸乙烯酯的加成反应。N-杂环化合物是由简单且可商购的起始原料在温和条件下以高收率合成的。