(5S)-1-benzyl-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-one | 1026910-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S)-1-benzyl-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-one
• CAS: 1026910-25-7
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: MQJDWPHLOVTYST-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-1-benzyl-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到(R)-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol
  参考文献：
  名称：

  Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology

  摘要：

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.097
• 作为产物：
  描述：

  N-benzyl-3-[(2R,3R)-3-phenyloxiran-2-yl]propanamide 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以89%的产率得到(5S)-1-benzyl-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology

  摘要：

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.097

文献信息

• Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology
  作者：Daniel P. Pienaar、Robin K. Mitra、Thomas I. van Deventer、Adriana L. Botes

  DOI：10.1016/j.tetlet.2008.08.097

  日期：2008.11

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.