methyl (E)-2-[bis(trimethylsilyloxy)amino]but-2-enoate | 304887-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (E)-2-[bis(trimethylsilyloxy)amino]but-2-enoate
• CAS: 304887-65-8
• 化学式: C₁₁H₂₅NO₄Si₂
• 分子量: 291.495
• InChiKey: FBEFEYQCVRGSID-MDZDMXLPSA-N

物化性质

• 沸点：
  276.9±42.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-[bis(trimethylsilyloxy)amino]but-2-enoate 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 methyl (Z)-2-(hydroxyimino)-3-(1H-imidazol-1-yl)butanoate
  参考文献：
  名称：

  Chemistry of N,N-Bis(silyloxy)enamines, Part 5

  摘要：

  Aliphatic nitro compounds can be considered as good precursors of a wide variety of alpha-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated alpha-azolyl-substituted oximes 6, which can be smoothly desilylated to give the target a-azolyl-substituted oximes 5. The mechanism of the key step of this process -N,C-coupling - includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well. The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the C=N bond in oximes was established by NMR.

  DOI：

  10.1002/1522-2675(200210)85:10<3489::aid-hlca3489>3.0.co;2-6
• 作为产物：
  描述：

  2-硝基丁酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 生成 methyl (E)-2-[bis(trimethylsilyloxy)amino]but-2-enoate
  参考文献：
  名称：

  N,N-双（甲硅烷氧基）烯胺的化学。第 8 部分：由脂肪族硝基化合物制备 α-叠氮基肟的一般方法

  摘要：

  介绍了一种通过中间体 N,N-双（硅氧基）烯胺从可用的脂肪族硝基化合物制备各种 α-羟基肟的新简便方法。讨论了关键步骤，N,N-双（甲硅烷氧基）烯胺重排的机理。

  DOI：

  10.1055/s-2005-861836

文献信息

• Synthesis of N,N-bis(silyloxy)enamines with a functionalized double bond
  作者：Alexander D. Dilman、Alexander A. Tishkov、Il’ya M. Lyapkalo、Sema L. Ioffe、Vadim V. Kachala、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1039/b004268o

  日期：——

  The general method for the double silylation of α- or β-functionalized aliphatic nitro compounds 1 leading to regio- and stereoselective formation of N,N-bis(silyloxy)enamines 3 with a functionalized double bond is elaborated. The configuration of obtained products is determined by NMR spectroscopy.

  详细阐述了 α- 或 β-官能化脂肪族硝基化合物 1 双硅烷基化，从而形成具有官能化双键的 N,N-双（硅烷氧基）烯胺 3 的区域和立体选择性的一般方法。 所获产物的构型由核磁共振光谱确定。
• Reactions of N,N-bis(siloxy)enamines with trimethylsilyl cyanide: aliphatic nitro compounds as convenient precursors of 5-aminoisoxazoles
  作者：Aleksei V. Lesiv、Sema L. Ioffe、Yurii A. Strelenko、Igor’ V. Bliznets、Vladimir A. Tartakovsky

  DOI：10.1070/mc2002v012n03abeh001585

  日期：2002.1

  A convenient procedure was developed for the synthesis of 5-aminoisoxazoles by the consecutive double silylation and cyanation of aliphatic nitro compounds.
• Chemistry of N,N-Bis(silyloxy)enamines, Part 5
  作者：Alexey V. Lesiv、Sema L. Ioffe、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1002/1522-2675(200210)85:10<3489::aid-hlca3489>3.0.co;2-6

  日期：2002.10

  Aliphatic nitro compounds can be considered as good precursors of a wide variety of alpha-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated alpha-azolyl-substituted oximes 6, which can be smoothly desilylated to give the target a-azolyl-substituted oximes 5. The mechanism of the key step of this process -N,C-coupling - includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well. The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the C=N bond in oximes was established by NMR.
• The Chemistry of<i>N</i>,<i>N</i>-Bis(siloxy)enamines. Part 8.A General Method for the Preparation of α-Azido Oximes from Aliphatic Nitro Compounds
  作者：Alexey V. Lesiv、Sema L. Ioffe、Alexey Yu. Sukhorokov、Igor V. Bliznets、Yulija A. Khomutova、Yuriy A. Strelenko

  DOI：10.1055/s-2005-861836

  日期：——

  A new convenient procedure for the preparation of a variety of α-hydroxy oximes from available aliphatic nitro compounds via intermediate N,N-bis(siloxy)enamines is presented. The mechanism of the key step, the rearrangement of N,N-bis(siloxy)en­amines, is discussed.

  介绍了一种通过中间体 N,N-双（硅氧基）烯胺从可用的脂肪族硝基化合物制备各种 α-羟基肟的新简便方法。讨论了关键步骤，N,N-双（甲硅烷氧基）烯胺重排的机理。