(R)-N-(5-(2-(4-hydroxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3,5-dioxopentyl)-6,6-dimethylheptanamide | 1190758-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-N-(5-(2-(4-hydroxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3,5-dioxopentyl)-6,6-dimethylheptanamide
• 英文别名: N-[5-[(2R)-2-[(4-hydroxyphenyl)methyl]-5-oxo-2H-pyrrol-1-yl]-3,5-dioxopentyl]-6,6-dimethylheptanamide
• CAS: 1190758-14-5
• 化学式: C₂₅H₃₄N₂O₅
• 分子量: 442.555
• InChiKey: JVYWPUPLDBDNFH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] carbonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以42%的产率得到(R)-N-(5-(2-(4-hydroxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3,5-dioxopentyl)-6,6-dimethylheptanamide
  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.