(R)-ypaoamide | 1190851-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-ypaoamide
• 英文别名: N-[(E)-5-[(2R)-2-[(4-hydroxyphenyl)methyl]-5-oxo-2H-pyrrol-1-yl]-3-methoxy-5-oxopent-3-enyl]-6,6-dimethylheptanamide
• CAS: 1190851-15-0
• 化学式: C₂₆H₃₆N₂O₅
• 分子量: 456.582
• InChiKey: ATTMLQCPKPSEGH-WDWWVRLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• Enantioselective Synthesis of the <i>R</i>-Enantiomer of the Feeding Deterrent (<i>S</i>)-Ypaoamide
  作者：Jie Chen、Pei-Qiang Huang、Yves Queneau

  DOI：10.1021/jo901557h

  日期：2009.10.2

  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.