pentafluorophenyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate | 1190758-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentafluorophenyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoate
• CAS: 1190758-11-2
• 化学式: C₂₁H₂₆F₅NO₄
• 分子量: 451.434
• InChiKey: PSAFUDLESHXSKE-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(4-(benzyloxy)-benzyl)-4-(benzyloxy)pyrrolidin-2-one 、 pentafluorophenyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以63%的产率得到N-[(E)-5-((2R,3S)-2-(4-(benzyloxy)benzyl)-3-(benzyloxy)-5-oxopyrrolidin-1-yl)-3-methoxy-5-oxopent-3-enyl]-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
• 作为产物：
  描述：

  五氟苯酚 、 (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到pentafluorophenyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate
  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.