3-(8-azido-1,4-dioxa-spiro[4.5]dec-8-yl)propionic acid ethyl ester | 686723-62-6

• 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: 3-(8-azido-1,4-dioxa-spiro[4.5]dec-8-yl)propionic acid ethyl ester
• 英文别名: ethyl 3-(8-azido-1,4-dioxaspiro[4.5]dec-8-yl)propanoate；ethyl 3-(8-azido-dioxaspiro[4.5]dec-8-yl)propanoate；Ethyl 3-(8-azido-1,4-dioxaspiro[4.5]decan-8-yl)propanoate
• CAS: 686723-62-6
• 化学式: C₁₃H₂₁N₃O₄
• 分子量: 283.327
• InChiKey: RXVDYOMYRSFQPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(8-azido-1,4-dioxa-spiro[4.5]dec-8-yl)propionic acid ethyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 40.0h， 以84%的产率得到1,4-二氧杂-9-氮杂二螺[4.2.4.2]十四烷-10-酮
  参考文献：
  名称：

  Radical Carboazidation:  Expedient Assembly of the Core Structure of Various Alkaloid Families

  摘要：

  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.

  DOI：

  10.1021/jo035843y
• 作为产物：
  描述：

  8-亚甲基-1,4-二噁螺[4.5]癸烷 、 碘代醋酸乙酯 在 苯磺酰基叠氮化物 、 六正丁基二锡 、 反式-二叔丁基连二次硝酸酯 作用下， 以 苯 为溶剂， 以80%的产率得到3-(8-azido-1,4-dioxa-spiro[4.5]dec-8-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Radical Carboazidation:  Expedient Assembly of the Core Structure of Various Alkaloid Families

  摘要：

  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.

  DOI：

  10.1021/jo035843y

文献信息

• Intramolecular Schmidt Reaction Involving Primary Azidoalcohols under Nonacidic Conditions: Synthesis of Indolizidine (−)-167B
  作者：Ajoy Kapat、Erich Nyfeler、Guy T. Giuffredi、Philippe Renaud

  DOI：10.1021/ja908933s

  日期：2009.12.16

  reported. This approach involves a nonacidic activation of the alcohol via triflation. The synthetic potential offered by the mild reaction conditions is demonstrated by a highly selective synthesis of (-)-indolizidine 167B.

  报道了从伯叠氮醇开始的强大的分子内施密特反应。该方法涉及通过三氟甲磺酸作用对醇进行非酸性活化。(-)-indolizidine 167B 的高选择性合成证明了温和反应条件提供的合成潜力。
• 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.