(3S)-3-羟基-1-(2-苯基乙基)吡咯烷-2,5-二酮 | 172276-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3S)-3-羟基-1-(2-苯基乙基)吡咯烷-2,5-二酮
• 英文名称: (3S)-3-Hydroxy-1-(2-phenylethyl)-2,5-pyrrolidinedione
• 英文别名: 2,5-Pyrrolidinedione, 3-hydroxy-1-(2-phenylethyl)-, (3S)-；(3S)-3-hydroxy-1-(2-phenylethyl)pyrrolidine-2,5-dione
• CAS: 172276-66-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: PEGBUFSLBLGCOS-JTQLQIEISA-N

物化性质

• 沸点：
  448.4±45.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-羟基-1-(2-苯基乙基)吡咯烷-2,5-二酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 79.0h， 生成 (-)-(10bS)-1,2,3,5,6,10b-Hexahydropyrrolo-<2,1-a>isoquinoline
  参考文献：
  名称：

  Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid

  摘要：

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.

  DOI：

  10.1021/jo00127a019
• 作为产物：
  描述：

  L-苹果酸 、 2-苯乙胺 以 xylene 为溶剂， 反应 3.5h， 以73%的产率得到(3S)-3-羟基-1-(2-苯基乙基)吡咯烷-2,5-二酮
  参考文献：
  名称：

  Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid

  摘要：

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.

  DOI：

  10.1021/jo00127a019

文献信息

• Asymmetric Synthesis of Furo-Pyrrolo-Isoquinoline and Furo-Indolizino-Indole Derivatives Via A Diastereoselective N-Acyliminium ion Cyclization
  作者：Lee, Yong Sup、Lee, Jae Yeol、Park, Hokoon

  DOI：10.1080/00397919708004155

  日期：1997.8

  Asymmetric synthesis of furo-pyrrolo-isoquinoline and furo-indolizino-indole derivatives via a diastereoselective N-acyliminium ion cyclization of chiral enamides is described. The requisite chiral enamides were prepared from readily available L-malic acid.
• Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid
  作者：Yong Sup Lee、Dong Wook Kang、Sook Ja Lee、Hokoon Park

  DOI：10.1021/jo00127a019

  日期：1995.11

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.