(S)-5-((R)-1-azidobut-3-enyl)-dihydrofuran-2(3H)-one | 1148034-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-5-((R)-1-azidobut-3-enyl)-dihydrofuran-2(3H)-one
• 英文别名: (5S)-5-[(1R)-1-azidobut-3-enyl]oxolan-2-one
• CAS: 1148034-82-5
• 化学式: C₈H₁₁N₃O₂
• 分子量: 181.194
• InChiKey: DGWBLBVLJMBMAG-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (S)-5-((R)-1-azidobut-3-enyl)-dihydrofuran-2(3H)-one 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (5R,6S)-6-allyl-5-hydroxypiperidin-2-one 、 (5S,6R)-6-allyl-5-hydroxypiperidin-2-one
  参考文献：
  名称：

  A concise enantioselective synthesis of (+)-febrifugine

  摘要：

  A short enantioselective synthesis of (+)-febrifugine, a potent antimalarial alkaloid, has been described based on the regioselective asymmetric dihydroxylation of a 1,4-dienic ester as the key step. The strategy also involves chemoselective [3,3]-sigmatropic rearrangement of 1,5-hexadiene-3-ol and intramolecular lactamization of azidolactone for the construction of piperidine core. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.024
• 作为产物：
  描述：

  (S)-1-((S)-tetrahydro-5-oxofuran-2-yl)but-3-enyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以87%的产率得到(S)-5-((R)-1-azidobut-3-enyl)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A concise enantioselective synthesis of (+)-febrifugine

  摘要：

  A short enantioselective synthesis of (+)-febrifugine, a potent antimalarial alkaloid, has been described based on the regioselective asymmetric dihydroxylation of a 1,4-dienic ester as the key step. The strategy also involves chemoselective [3,3]-sigmatropic rearrangement of 1,5-hexadiene-3-ol and intramolecular lactamization of azidolactone for the construction of piperidine core. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.024

文献信息

• A concise enantioselective synthesis of (+)-febrifugine
  作者：Lourdusamy Emmanuvel、Dayanand A. Kamble、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2008.11.024

  日期：2009.1

  A short enantioselective synthesis of (+)-febrifugine, a potent antimalarial alkaloid, has been described based on the regioselective asymmetric dihydroxylation of a 1,4-dienic ester as the key step. The strategy also involves chemoselective [3,3]-sigmatropic rearrangement of 1,5-hexadiene-3-ol and intramolecular lactamization of azidolactone for the construction of piperidine core. (C) 2008 Elsevier Ltd. All rights reserved.