(E)-ethyl 2-(methoxyimino)acetate | 68786-31-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-ethyl 2-(methoxyimino)acetate
• 英文别名: Methoxyiminoacetic acid ethyl ester；ethyl (2E)-2-methoxyiminoacetate
• CAS: 68786-31-2
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: YXJZAMRXWYECTM-GQCTYLIASA-N

物化性质

• 沸点：
  147.6±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(methoxyimino)acetate 在 Hoveyda-Grubbs catalyst second generation 、 氯化铵 、 三乙胺 、 对苯醌 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 19.0h， 生成 ethyl 5-(1,3-dioxoisoindolin-2-yl)-1-methoxy-3-methyl-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

  摘要：

  The synthesis of the potent antitumor agent (+/-)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

  DOI：

  10.1021/ja207835w
• 作为产物：
  描述：

  乙醛酸乙酯 、 甲氧基胺盐酸盐 在 吡啶 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 15.0h， 生成 (E)-ethyl 2-(methoxyimino)acetate
  参考文献：
  名称：

  Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

  摘要：

  The synthesis of the potent antitumor agent (+/-)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

  DOI：

  10.1021/ja207835w

文献信息

• Synthesis of 2‐Azanorbornanes via Strain‐Release Formal Cycloadditions Initiated by Energy Transfer
  作者：Yu‐Che Chang、Christophe Salome、Thomas Fessard、M. Kevin Brown

  DOI：10.1002/anie.202314700

  日期：2023.12.18

  Rigid bicycles are becoming more popular in the pharmaceutical industry because they allow for expansion to new and unique chemical spaces. This work describes a new strategy to construct 2‐azanorbornanes, which can act as rigid piperidine/pyrrolidine scaffolds with well‐defined exit vectors. To achieve the synthesis of 2‐azanorbornanes, new strain‐release reagent, azahousane, is introduced along with its photosensitized strain‐release formal cycloaddition with alkenes. Furthermore, new reactivity between a housane and an imine is disclosed. Both strategies lead to various substituted 2‐azanorbornanes with good selectivities.

  摘要刚性自行车在制药行业越来越受欢迎，因为它们可以扩展到新的独特的化学空间。这项工作描述了一种构建 2-azanorbornanes 的新策略，它可以作为具有明确出口载体的刚性哌啶/吡咯烷支架。为了合成 2-氮杂降冰片烷，引入了新的应变释放试剂氮杂环烷及其与烯烃的光敏应变释放正式环化反应。此外，研究还揭示了一种新的反应性。这两种策略都能产生具有良好选择性的各种取代的 2-氮杂降冰片烷。
• Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis
  作者：Timothy J. Donohoe、Christopher R. Jones、Luiz C. A. Barbosa

  DOI：10.1021/ja207835w

  日期：2011.10.19

  The synthesis of the potent antitumor agent (+/-)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.