Z-methyl 5-allylamino-4,4-dimethyl-2-methoxypent-2-enoate | 769939-31-3

• 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: Z-methyl 5-allylamino-4,4-dimethyl-2-methoxypent-2-enoate
• 英文别名: methyl (Z)-2-methoxy-4,4-dimethyl-5-(prop-2-enylamino)pent-2-enoate
• CAS: 769939-31-3
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: XQCHGUPJUKGEHN-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-methyl 5-allylamino-4,4-dimethyl-2-methoxypent-2-enoate 在 硫酸 、 sodium hydroxide 、 水 作用下， 反应 1.0h， 以81%的产率得到5,5-Dimethyl-1-prop-2-enylpiperidine-2,3-dione
  参考文献：
  名称：

  Synthesis of Novel 3-Oxopiperidin-2-ones from Methyl 2-Alkoxy-5-amino-2-pentenoates

  摘要：

  在甲醇中用甲醇钠处理 4-(1-氯-1-甲基乙基)-或 4-(2-卤-1,1-二甲基乙基)氮杂环丁-2-酮后，烷基氨基取代的 2-烷氧基-2-戊烯酸酯被评估为环化生成吡咯烷和哌啶的底物。因此，本文介绍了一种利用过量浓硫酸将 2-烷氧基-5-氨基-4,4-二甲基-2-戊烯酸甲酯转化为 5,5-二甲基-3-氧代哌啶-2-酮的简便方法。

  DOI：

  10.1055/s-2008-1077970
• 作为产物：
  描述：

  cis-1-allyl-4-[(2-chloro-1,1-dimethyl)ethyl]-3-methoxyazetidin-2-one 、 甲醇 在 sodium methylate 作用下， 反应 4.0h， 以60%的产率得到Z-methyl 5-allylamino-4,4-dimethyl-2-methoxypent-2-enoate
  参考文献：
  名称：

  Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines

  摘要：

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.

  DOI：

  10.1021/jo040161b

文献信息

• Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines
  作者：Yves Dejaegher、Norbert De Kimpe

  DOI：10.1021/jo040161b

  日期：2004.9.1

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.
• Synthesis of Novel 3-Oxopiperidin-2-ones from Methyl 2-Alkoxy-5-amino-2-pentenoates
  作者：Norbert De Kimpe、Yves Dejaegher、Matthias D’hooghe

  DOI：10.1055/s-2008-1077970

  日期：——

  Alkylamino-substituted 2-alkoxy-2-pentenoates, obtained through ring transformation of 4-(1-chloro-1-methylethyl)- or 4-(2-halo-1,1-dimethylethyl)azetidin-2-ones upon treatment with sodium methoxide in methanol, have been evaluated as substrates for the cyclization towards pyrrolidines and piperidines. Thus, a convenient approach for the transformation of methyl 2-alkoxy-5-amino-4,4-dimethyl-2-pentenoates into 5,5-dimethyl-3-oxopiperidin-2-ones is described utilizing an excess of concentrated sulfuric acid.

  在甲醇中用甲醇钠处理 4-(1-氯-1-甲基乙基)-或 4-(2-卤-1,1-二甲基乙基)氮杂环丁-2-酮后，烷基氨基取代的 2-烷氧基-2-戊烯酸酯被评估为环化生成吡咯烷和哌啶的底物。因此，本文介绍了一种利用过量浓硫酸将 2-烷氧基-5-氨基-4,4-二甲基-2-戊烯酸甲酯转化为 5,5-二甲基-3-氧代哌啶-2-酮的简便方法。