(S)-1,3-dibenzyloxypyrrolidin-2,5-dione | 1241920-51-3

• 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: (S)-1,3-dibenzyloxypyrrolidin-2,5-dione
• 英文别名: (S)-O,O'-bisbenzyl-1-hydroxymalimide；(3S)-1,3-bis(phenylmethoxy)pyrrolidine-2,5-dione
• CAS: 1241920-51-3
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: KGMCFSJLBMWAQZ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1,3-dibenzyloxypyrrolidin-2,5-dione 、 异丙基溴化镁 在 氯化铵 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以73%的产率得到(4S,5R)-1,4-dibenzyloxy-5-isopropylpyrrolidin-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
• 作为产物：
  描述：

  (S)-2-(benzyloxy)butane-1,4-diol 、 苄氧基胺盐酸盐 在 乙酰氯 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到(S)-1,3-dibenzyloxypyrrolidin-2,5-dione
  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