ethyl 4-azido-8-bromooctanoate | 499968-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-azido-8-bromooctanoate
• 英文别名: Ethyl 4-azido-8-bromooctanoate
• CAS: 499968-85-3
• 化学式: C₁₀H₁₈BrN₃O₂
• 分子量: 292.176
• InChiKey: BJRDTSQUEMXHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-azido-8-bromooctanoate 在 indium 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Radical Carboazidation of Alkenes: An Efficient Tool for the Preparation of Pyrrolidinone Derivatives

  摘要：

  DOI：

  10.1002/1521-3773(20020916)41:18<3460::aid-anie3460>3.0.co;2-6
• 作为产物：
  描述：

  ethyl 2-(azidosulfonyl)acetate 、 6-溴-1-己烯 在 偶氮叔丁烷 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以90%的产率得到ethyl 4-azido-8-bromooctanoate
  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

• 3-Pyridinesulfonyl Azide: A Useful Reagent for Radical Azidation
  作者：Philippe Panchaud、Philippe Renaud

  DOI：10.1002/adsc.200404038

  日期：2004.7

  Radical azidations and carboazidations have been achieved using 3-pyridinesulfonyl azide as azidating agent. Due to its base properties and its polarity, the excess of reagent is readily removed at the end of the reaction by filtration through silica gel or by extraction with either aqueous 1 M HCl or 1 M CuSO4. The use of this reagent greatly facilitates the tedious purifications of the final azides

  使用3-吡啶磺酰基叠氮化物作为叠氮化剂已经实现了自由基叠氮化和碳叠氮化。由于其碱性和极性，在反应结束时，可以通过硅胶过滤或用1 M HCl水溶液或1 M CuSO 4水溶液萃取来轻松除去过量的试剂。当根据涉及苯磺酰叠氮化物的原始方法进行反应时，该试剂的使用极大地简化了最终叠氮化物的乏味纯化。
• Radical Carboazidation:  Expedient Assembly of the Core Structure of Various Alkaloid Families
  作者：Philippe Panchaud、Cyril Ollivier、Philippe Renaud、Sarunas Zigmantas

  DOI：10.1021/jo035843y

  日期：2004.4.1

  A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is also described. These compounds are important building blocks for the synthesis of numerous alkaloids such as, for instance, FR901483.
• Radical Carboazidation of Alkenes: An Efficient Tool for the Preparation of Pyrrolidinone Derivatives
  作者：Philippe Renaud、Cyril Ollivier、Philippe Panchaud

  DOI：10.1002/1521-3773(20020916)41:18<3460::aid-anie3460>3.0.co;2-6

  日期：2002.9.16
• 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.