4-[((2R,3S)-3-acetoxy-1-((E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxopyrrolidin-2-yl)methyl]phenyl acetate | 1190758-16-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[((2R,3S)-3-acetoxy-1-((E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxopyrrolidin-2-yl)methyl]phenyl acetate
• 英文别名: [(2R,3S)-2-[(4-acetyloxyphenyl)methyl]-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxopyrrolidin-3-yl] acetate
• CAS: 1190758-16-7
• 化学式: C₃₀H₄₂N₂O₈
• 分子量: 558.672
• InChiKey: CODJSIQJBYMDNW-GQMHNCHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[((2R,3S)-3-acetoxy-1-((E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxopyrrolidin-2-yl)methyl]phenyl acetate 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到rac-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：

  N-[(E)-5-((2R,3S)-2-(4-hydroxybenzyl)-3-hydroxy-5-oxopyrrolidin-1-yl)-3-methoxy-5-oxopent-3-enyl]-6,6-dimethylheptanamide 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以94%的产率得到4-[((2R,3S)-3-acetoxy-1-((E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoyl)-5-oxopyrrolidin-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