(2R,5S)-2-but-3-en-1-yl-5-phenylpyrrolidine | 1109109-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,5S)-2-but-3-en-1-yl-5-phenylpyrrolidine
• 英文别名: (2R,5S)-2-but-3-enyl-5-phenylpyrrolidine
• CAS: 1109109-80-9
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: XFMMYCXGAYTDKI-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 (2R,5S)-2-but-3-en-1-yl-5-phenylpyrrolidine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到(3S,5R,7aS)-3-phenyl-5-[(phenylseleno)methyl]hexahydro-1H-pyrrolizine
  参考文献：
  名称：

  Selenium-promoted synthesis of enantiopure octahydroindolizines, hexahydro-1H-pyrrolizines and hexahydro-3H-pyrrolizin-3-ones

  摘要：

  Enantiomerically pure disubstituted pyrrolidines, recently synthesized from commercially available enantiomerically pure beta-aminoalcohol, were used as starting materials to synthesize enantiomerically pure hexahydro-1H-pyrrolizines and octahydroindolizine through a cyclization reaction promoted by N-(phenylseleno)phthalimide. Similarly, starting from enantiopure 5-(hydroxymethyl)pyrrolidin-2-ones, enantiopure hexahydro-3H-pyrrolizin-3-ones were obtained. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.006
• 作为产物：
  描述：

  (2S,5S)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine 、 烯丙基三丁基锡 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 以68%的产率得到(2R,5S)-2-but-3-en-1-yl-5-phenylpyrrolidine
  参考文献：
  名称：

  Selenium-promoted synthesis of enantiopure octahydroindolizines, hexahydro-1H-pyrrolizines and hexahydro-3H-pyrrolizin-3-ones

  摘要：

  Enantiomerically pure disubstituted pyrrolidines, recently synthesized from commercially available enantiomerically pure beta-aminoalcohol, were used as starting materials to synthesize enantiomerically pure hexahydro-1H-pyrrolizines and octahydroindolizine through a cyclization reaction promoted by N-(phenylseleno)phthalimide. Similarly, starting from enantiopure 5-(hydroxymethyl)pyrrolidin-2-ones, enantiopure hexahydro-3H-pyrrolizin-3-ones were obtained. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.006

文献信息

• Selenium-promoted synthesis of enantiopure octahydroindolizines, hexahydro-1H-pyrrolizines and hexahydro-3H-pyrrolizin-3-ones
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Catalina Scarponi

  DOI：10.1016/j.tetasy.2008.10.006

  日期：2008.10

  Enantiomerically pure disubstituted pyrrolidines, recently synthesized from commercially available enantiomerically pure beta-aminoalcohol, were used as starting materials to synthesize enantiomerically pure hexahydro-1H-pyrrolizines and octahydroindolizine through a cyclization reaction promoted by N-(phenylseleno)phthalimide. Similarly, starting from enantiopure 5-(hydroxymethyl)pyrrolidin-2-ones, enantiopure hexahydro-3H-pyrrolizin-3-ones were obtained. (C) 2008 Elsevier Ltd. All rights reserved.