Ethyl 3-azido-2-oxooxolane-3-carboxylate | 1189109-61-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 3-azido-2-oxooxolane-3-carboxylate
• 英文别名: ethyl 3-azido-2-oxooxolane-3-carboxylate
• CAS: 1189109-61-2
• 化学式: C₇H₉N₃O₄
• 分子量: 199.166
• InChiKey: UFFRQKXQDNDFDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 2-氧代四氢呋喃-3-羧酸乙酯 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以38%的产率得到Ethyl 3-azido-2-oxooxolane-3-carboxylate
  参考文献：
  名称：

  Azidation of β-carbonyl lactones and lactams

  摘要：

  The direct azidation of various heterocyclic beta-ketoesters, lactones, and lactams is reported. By using tosylazide and an organic base such as L-proline or TBD, the direct alpha-insertion of azide into these substrates was achieved in moderate to good yields, without competitive deacylating diazo transfer. This procedure represents an interesting alternative to the usual two-step approach of alpha-halogenation and subsequent displacement with azide ion. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.039

文献信息

• Azidation of β-carbonyl lactones and lactams
  作者：Dhurke Kashinath、Ghyslain Budin、Rachid Baati、Stéphane Meunier、Alain Wagner

  DOI：10.1016/j.tetlet.2009.07.039

  日期：2009.9

  The direct azidation of various heterocyclic beta-ketoesters, lactones, and lactams is reported. By using tosylazide and an organic base such as L-proline or TBD, the direct alpha-insertion of azide into these substrates was achieved in moderate to good yields, without competitive deacylating diazo transfer. This procedure represents an interesting alternative to the usual two-step approach of alpha-halogenation and subsequent displacement with azide ion. (C) 2009 Elsevier Ltd. All rights reserved.