3-(3',6'-Dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropanoic acid N-(4-hydroxyl)butylamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(3',6'-Dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropanoic acid N-(4-hydroxyl)butylamide
• 英文别名: 3-(2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-N-(4-hydroxybutyl)-3-methylbutanamide
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: NDJNXHZPTKVMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基-1-丁醇 、 3-(2,4-二甲基-3,6-二氧代-1-环己-1,4-二烯基)-3-甲基丁酸 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以97%的产率得到3-(3',6'-Dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropanoic acid N-(4-hydroxyl)butylamide
  参考文献：
  名称：

  Development of a Novel Redox-Sensitive Protecting Group for Amines Which Utilizes a Facilitated Lactonization Reaction

  摘要：

  Selective protection and deprotection of functional groups are essential components of modern organic and peptide synthesis. To cope with the demand for the synthesis of organic molecules and peptides with increasing complexity, there has been a need to develop novel protecting groups which are readily cleavable under fundamentally different conditions to ensure selective modifications of specified functional groups. This report is focused on the development of a redox-sensitive amine protecting group using a substituted quinone propionic acid (1a). The key feature of this protecting group is that upon reduction of the quinone 1 to the hydroquinone 2, it undergoes a spontaneous lactonization to release the functional group attached to the carboxyl group (HXR). High yields were achieved for both the protection and deprotection reactions, and the reduction conditions required for the deprotection are very mild (Na2S2O4 or electrochemically) and thus very compatible with most functional groups encountered in organic molecules and peptides.

  DOI：

  10.1021/jo00108a013

文献信息

• Development of a Novel Redox-Sensitive Protecting Group for Amines Which Utilizes a Facilitated Lactonization Reaction
  作者：Binghe Wang、Siming Liu、Ronald T. Borchardt

  DOI：10.1021/jo00108a013

  日期：1995.2

  Selective protection and deprotection of functional groups are essential components of modern organic and peptide synthesis. To cope with the demand for the synthesis of organic molecules and peptides with increasing complexity, there has been a need to develop novel protecting groups which are readily cleavable under fundamentally different conditions to ensure selective modifications of specified functional groups. This report is focused on the development of a redox-sensitive amine protecting group using a substituted quinone propionic acid (1a). The key feature of this protecting group is that upon reduction of the quinone 1 to the hydroquinone 2, it undergoes a spontaneous lactonization to release the functional group attached to the carboxyl group (HXR). High yields were achieved for both the protection and deprotection reactions, and the reduction conditions required for the deprotection are very mild (Na2S2O4 or electrochemically) and thus very compatible with most functional groups encountered in organic molecules and peptides.