ethyl 2-(azidosulfonyl)acetate | 1258206-60-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: ethyl 2-(azidosulfonyl)acetate
• 英文别名: ethyl 2-(azidosulfonyl)ethanoate；Ethyl 2-azidosulfonylacetate
• CAS: 1258206-60-8
• 化学式: C₄H₇N₃O₄S
• 分子量: 193.183
• InChiKey: CJWQVRDXTMLVET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(azidosulfonyl)acetate 、 亚甲基环己烷 在 偶氮叔丁烷 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以92%的产率得到ethyl 3-(1-azidocyclohexyl)propanoate
  参考文献：
  名称：

  Efficient Carboazidation of Alkenes Using a Radical Desulfonylative Azide Transfer Process

  摘要：

  The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.

  DOI：

  10.1021/ja1068036
• 作为产物：
  描述：

  (氯磺酰基)乙酸乙酯 在 sodium azide 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以60%的产率得到ethyl 2-(azidosulfonyl)acetate
  参考文献：
  名称：

  Efficient Carboazidation of Alkenes Using a Radical Desulfonylative Azide Transfer Process

  摘要：

  The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.

  DOI：

  10.1021/ja1068036

文献信息

• Efficient Carboazidation of Alkenes Using a Radical Desulfonylative Azide Transfer Process
  作者：Karin Weidner、André Giroult、Philippe Panchaud、Philippe Renaud

  DOI：10.1021/ja1068036

  日期：2010.12.15

  The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.