2-oxo-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester | 49613-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 2-oxo-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester
• 英文别名: 7-Carboethoxy-7-azabicyclo<4.1.0>heptane-2-one；2-Oxo-7-azabicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester；ethyl 2-oxo-7-azabicyclo[4.1.0]heptane-7-carboxylate
• CAS: 49613-90-3
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: XWXRKEJXGUBEFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 ethyl N-(tosyloxy)carbamate 在 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40%的产率得到2-oxo-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Aziridination of α,β-unsaturated ketones

  摘要：

  alpha,beta-Unsaturated ketones are aziridinated by [(arenesulphonyl)oxy]carbamates and CaO (or Cs2CO3) or by N3CO2Et photolysis. A remote chiral center induced up to 74% de. Bis-unsaturated substrates showed scarce regioselectivity under all conditions. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0040-4020(98)00870-9

文献信息

• A solvent-free amidation of vinylogous esters via direct aziridination
  作者：Emily C. McLaughlin、Anuska Shrestha、Madison H. Fletcher、Nathaniel S. Steinauer、Min Kyung Shinn、Sabrina M. Shahid

  DOI：10.1016/j.tetlet.2013.07.135

  日期：2013.10

  A microwave-mediated aziridination of α,β-unsaturated ketones and esters through the decomposition of ethyl azidoformate has been developed. When the same atom-economical reaction conditions are applied to cyclic vinylogous esters, N-functionalization at the α-position occurs. Based on NMR analysis, these amidation products appear to be formed from the desired aziridine in moderate to good yields.

  通过叠氮甲酸乙酯的分解，对α，β-不饱和酮和酯进行了微波介导的叠氮化。当将相同的原子经济反应条件应用于环状乙烯基酯时，在α位发生N-官能化。基于NMR分析，这些酰胺化产物似乎由所需的氮丙啶以中等至良好的产率形成。
• A facile aziridination of allylic and homoallylic cyclic acetals
  作者：Stefania Fioravanti、M. Antonietta Loreto、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/s0040-4039(00)79349-x

  日期：1993.7

  Easy and fast aziridination of allylic and homoallylic acetals 2a, 2b and 2c has been achieved by NsONHCO2Et in the presence of solid K2CO3.
• Aziridination of α,β-unsaturated ketones
  作者：Stefania Fioravanti、Lucio Pellacani、Stefania Tabanella、Paolo A. Tardella

  DOI：10.1016/s0040-4020(98)00870-9

  日期：1998.11

  alpha,beta-Unsaturated ketones are aziridinated by [(arenesulphonyl)oxy]carbamates and CaO (or Cs2CO3) or by N3CO2Et photolysis. A remote chiral center induced up to 74% de. Bis-unsaturated substrates showed scarce regioselectivity under all conditions. (C) 1998 Elsevier Science Ltd. AII rights reserved.

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