ethyl 4-azidodecanoate | 499968-75-1

• 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-azidodecanoate
• CAS: 499968-75-1
• 化学式: C₁₂H₂₃N₃O₂
• 分子量: 241.334
• InChiKey: KVMPVABGPXJXGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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-azidodecanoate 在 indium 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成 4-Amino-decanoic acid ethyl ester
  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：

  2-((乙氧基碳硫代)硫代)乙酸乙酯 、 辛烯 在 苯磺酰基叠氮化物 、 air 、 三乙基硼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.25h， 以51%的产率得到ethyl 4-azidodecanoate
  参考文献：
  名称：

  自由基碳叠氮化和叠氮化的便捷无锡工艺

  摘要：

  以三乙基硼烷为引发剂在水中实现了烯烃的自由基碳叠氮化。在开放系统中，室温下1小时内即可完成此高效过程。这些新的无锡碳叠氮化条件对环境友好，并允许与过量的烯烃或自由基前体进行反应。它们也适用于烷基碘的简单自由基叠氮化以及涉及环化过程的更复杂的级联反应。

  DOI：

  10.1021/jo0498720

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。
• Tin-Free Radical Carboazidation
  作者：Philippe Panchaud、Philippe Renaud

  DOI：10.2533/000942904777677920

  日期：——

  The radical carboazidation of alkenes could be achieved in water using triethylborane as initiator. This efficient process is complete in one hour at room temperature in an open system. These new tin-free azidation and carboazidation conditions are environmentally friendly and enable reactions to be run with an excess of either the alkene or the radical precursor. Furthermore, 3-pyridinesulfonyl azide could be used in order to avoid tedious purifications, especially when the reaction product has a similar chromatographic behavior to benzenesulfonyl azide, our original azidation reagent.

  烯烃的基础碳酰肼化反应可以在水中使用三乙基硼烷作为引发剂实现。这种高效的过程在常温下在开放系统中一个小时内完成。这些新的无锡碳酰肼化条件对环境友好，并且能够使用烯烃或自由基前体的过量反应。此外，3-吡啶磺酰肼可以用于避免繁琐的纯化，特别是当反应产物具有类似苯磺酰肼的色谱行为时，我们的原始肼化试剂。
• 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.
• 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.
• 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