(S)-5-((S)-azido(phenyl)methyl)-dihydrofuran-2(3H)-one | 1068141-88-7

• 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-((S)-azido(phenyl)methyl)-dihydrofuran-2(3H)-one
• 英文别名: (5S)-5-[(S)-azido(phenyl)methyl]oxolan-2-one
• CAS: 1068141-88-7
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: VVNGHEGEEGVWKC-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-((S)-azido(phenyl)methyl)-dihydrofuran-2(3H)-one 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91%的产率得到(5S,6S)-5-hydroxy-6-phenylpiperidin-2-one
  参考文献：
  名称：

  A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate

  摘要：

  A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a delta-azidolactone was used in the construction of the piperidine moiety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.086
• 作为产物：
  描述：

  [(R)-[(2S)-5-oxooxolan-2-yl]-phenylmethyl] methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以94%的产率得到(S)-5-((S)-azido(phenyl)methyl)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate

  摘要：

  A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a delta-azidolactone was used in the construction of the piperidine moiety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.086

文献信息

• Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction
  作者：Sunil V. Pansare、Eldho K. Paul

  DOI：10.1039/c2ob06644k

  日期：——

  The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

  从γ-克罗通内酯和苯甲醛的有机催化直接维尼洛格斯阿尔多尔反应中获得的γ-丁内酯，作为合成目标2,3-二取代吡啶的关键起始材料，经过高效合成得到3-羟基-2-苯基呱啶中间体。