(4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone | 253608-06-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone
• 英文别名: (4S,5R)-1-benzyl-4-hydroxy-5-phenylsulfanylpyrrolidin-2-one
• CAS: 253608-06-9
• 化学式: C₁₇H₁₇NO₂S
• 分子量: 299.393
• InChiKey: VTIFHZLTIYTIES-DOTOQJQBSA-N

物化性质

• 沸点：
  537.7±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone 在 正丁基锂 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以86.6%的产率得到(S)-1-苄基-4-羟基-2-吡咯烷酮
  参考文献：
  名称：

  A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues

  摘要：

  Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy-3-substituted 2-pyrrolidinones in one-pot and in high regio- and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy-2-pyrrolidinone using LN afforded naturally occurring (-)-(S)-4-hydroxy-2-pyrrolidinone. (-)-(3S,4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the y-amino acid residue found in marine natural products, bistramides, was prepared by the same method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00321-3
• 作为产物：
  描述：

  (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 (4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone
  参考文献：
  名称：

  A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues

  摘要：

  Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy-3-substituted 2-pyrrolidinones in one-pot and in high regio- and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy-2-pyrrolidinone using LN afforded naturally occurring (-)-(S)-4-hydroxy-2-pyrrolidinone. (-)-(3S,4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the y-amino acid residue found in marine natural products, bistramides, was prepared by the same method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00321-3

文献信息

• A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
  作者：Pei Qiang Huang、Xiao Zheng、Shi Li Wang、Jian Liang Ye、Li Ren Jin、Zhong Chen

  DOI：10.1016/s0957-4166(99)00321-3

  日期：1999.8

  Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy-3-substituted 2-pyrrolidinones in one-pot and in high regio- and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy-2-pyrrolidinone using LN afforded naturally occurring (-)-(S)-4-hydroxy-2-pyrrolidinone. (-)-(3S,4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the y-amino acid residue found in marine natural products, bistramides, was prepared by the same method. (C) 1999 Elsevier Science Ltd. All rights reserved.