ethyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate | 1190758-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate
• 英文别名: ethyl (E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoate
• CAS: 1190758-09-8
• 化学式: C₁₇H₃₁NO₄
• 分子量: 313.437
• InChiKey: YADGGJWAUHCSOW-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-(6,6-dimethylheptanamido)-3-methoxypent-2-enoate 在 盐酸 、 水 作用下， 生成 ethyl 5-(6,6-dimethylheptanamido)-3-oxopentanoate
  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：

  ethyl 5-(6,6-dimethylheptanamido)-3-oxopentanoate 、 原甲酸三甲酯 在 硫酸 作用下， 反应 96.0h， 以71%的产率得到ethyl (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.