(R,E)-4-[(1-(5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]phenyl acetate | 1190851-17-2

• 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: (R,E)-4-[(1-(5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]phenyl acetate
• 英文别名: [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] acetate
• CAS: 1190851-17-2
• 化学式: C₂₈H₃₈N₂O₆
• 分子量: 498.62
• InChiKey: HUXZPDSLMXPVRL-FRSADPSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R,E)-4-[(1-(5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]phenyl acetate 在 Candida cylindracea lipase 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以44%的产率得到(R)-ypaoamide
  参考文献：
  名称：

  Enantioselective Synthesis of the R-Enantiomer of the Feeding Deterrent (S)-Ypaoamide

  摘要：

  The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.

  DOI：

  10.1021/jo901557h
• 作为产物：
  描述：

  4-[((2R,3S)-1-((E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-3-hydroxy-5-oxopyrrolidin-2-yl)methyl]phenyl acetate 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以73%的产率得到(R,E)-4-[(1-(5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]phenyl acetate
  参考文献：
  名称：

  Enantioselective Synthesis of the R-Enantiomer of the Feeding Deterrent (S)-Ypaoamide

  摘要：

  The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.

  DOI：

  10.1021/jo901557h