(4S,5R)-4-benzyloxy-5-phenylpyrrolidin-2-one | 1241920-87-5

• 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: (4S,5R)-4-benzyloxy-5-phenylpyrrolidin-2-one
• 英文别名: (4S,5R)-5-phenyl-4-phenylmethoxypyrrolidin-2-one
• CAS: 1241920-87-5
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: WTQWYTYYIWCESN-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4S,5R)-1,4-dibenzyloxy-5-phenylpyrrolidin-2-one 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(4S,5R)-4-benzyloxy-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

  摘要：

  O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.063

文献信息

• N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B
  作者：Zhao-Bao Ye、Jie Chen、Wei-Hua Meng、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2010.04.063

  日期：2010.4

  O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.