(2S,5R)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine | 1004993-39-8

• 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: (2S,5R)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine
• 英文别名: (2S,5R)-2-phenyl-5-(phenylselanylmethyl)pyrrolidine
• CAS: 1004993-39-8
• 化学式: C₁₇H₁₉NSe
• 分子量: 316.305
• InChiKey: HXHBNMJDRZVHOP-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (2S,5R)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以72%的产率得到cis-2-Methyl-5-phenylpyrrolidine
  参考文献：
  名称：

  Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols

  摘要：

  Starting from commercially available enantiomerically pure aminoalcohols and using simple conversions promoted by organoselenium reagents, several enantiomerically pure substituted pyrrolidines were prepared. After double protections (R)- or (S)-2-phenylglycinols were converted into the beta-amino selenides by displacing the tosyl group with phenyl selenolate anions. The phenylseleno group was then substituted by an allyl group by treatment with allyltributyltin and AIBN. The reaction of these allylic derivatives with electrophilic phenylselenium reagents afforded selenium containing pyrrolidines as the result of a 5-exo-trig cyclization. The pyrrolidine derivatives thus obtained were reductively deselenylated with triphenyltin hydride and AIBN. Moreover, the selenides were converted into the selenones, which easily gave substitution with different nucleophiles. Enantiopure 2,5-pyrrolidines containing azido, methylthio, cyano and iodo groups were thus obtained. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.003
• 作为产物：
  描述：

  tert-butyl [(1S)-1-phenylpent-4-en-1-yl]carbamate 、 N-(苯硒基)邻苯二甲酰亚胺 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,5S)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine 、 (2S,5R)-2-phenyl-5-[(phenylseleno)methyl]pyrrolidine
  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.
• Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Catalina Scarponi、Andrea Temperini、Francesca Marini、Claudio Santi

  DOI：10.1016/j.tetasy.2007.11.003

  日期：2007.11

  Starting from commercially available enantiomerically pure aminoalcohols and using simple conversions promoted by organoselenium reagents, several enantiomerically pure substituted pyrrolidines were prepared. After double protections (R)- or (S)-2-phenylglycinols were converted into the beta-amino selenides by displacing the tosyl group with phenyl selenolate anions. The phenylseleno group was then substituted by an allyl group by treatment with allyltributyltin and AIBN. The reaction of these allylic derivatives with electrophilic phenylselenium reagents afforded selenium containing pyrrolidines as the result of a 5-exo-trig cyclization. The pyrrolidine derivatives thus obtained were reductively deselenylated with triphenyltin hydride and AIBN. Moreover, the selenides were converted into the selenones, which easily gave substitution with different nucleophiles. Enantiopure 2,5-pyrrolidines containing azido, methylthio, cyano and iodo groups were thus obtained. (c) 2007 Elsevier Ltd. All rights reserved.