methyl 3-cyano-3-methylbutanoate | 132218-55-4

• 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: methyl 3-cyano-3-methylbutanoate
• 英文别名: Methyl 3-cyano-3,3-dimethylpropanoate
• CAS: 132218-55-4
• 化学式: C₇H₁₁NO₂
• mdl: MFCD28145379
• 分子量: 141.17
• InChiKey: YLMVBVOUQGVTGX-UHFFFAOYSA-N

物化性质

• 沸点：
  221.9±23.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-cyano-3-methylbutanoate 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 生成 2,2-二甲基琥珀酸
  参考文献：
  名称：

  Derbesy,M. et al., Bulletin de la Societe Chimique de France, 1971, # 5, p. 1789 - 1793

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,2-dimethyl-3-(trimethylsiloxy)-1-cyclopropanecarboxylate 在 甲酸 、 盐酸羟胺 作用下， 反应 6.0h， 以54%的产率得到methyl 3-cyano-3-methylbutanoate
  参考文献：
  名称：

  One-Pot Generation of C≡X Bonds from Methyl 2-Siloxycyclopropane­carboxylates: Simple Syntheses of Functionalized Nitriles and Alkynes

  摘要：

  Starting from methyl 2-siloxycyclopropanecarboxylates simple and efficient one-pot procedures are described that lead to beta-cyanoesters and methoxycarbonyl-substituted terminal alkynes. The prepared functionalized alkynes were subjected to typical transformations such as [3+2] cycloaddition providing triazole derivatives, Sonogashira coupling, Au-catalyzed hydrophosphorylation or a copper-catalyzed coupling of methyl diazoacetate furnishing alkyne 14 and allene derivative 15. The Pauson-Khand reaction of the enyne 4c afforded a diastereomeric mixture of methyl 5-oxohexahydropentalen-2-carboxylate 16 in moderate yield.

  DOI：

  10.1055/s-0034-1378370

文献信息

• Derbesy,M. et al., Bulletin de la Societe Chimique de France, 1971, # 5, p. 1789 - 1793
  作者：Derbesy,M. et al.

  DOI：——

  日期：——
• One-Pot Generation of C≡X Bonds from Methyl 2-Siloxycyclopropane­carboxylates: Simple Syntheses of Functionalized Nitriles and Alkynes
  作者：Reinhold Zimmer、Hans-Ulrich Reissig、Dorian Reich、Dennis Müller、Luise Schefzig

  DOI：10.1055/s-0034-1378370

  日期：——

  Starting from methyl 2-siloxycyclopropanecarboxylates simple and efficient one-pot procedures are described that lead to beta-cyanoesters and methoxycarbonyl-substituted terminal alkynes. The prepared functionalized alkynes were subjected to typical transformations such as [3+2] cycloaddition providing triazole derivatives, Sonogashira coupling, Au-catalyzed hydrophosphorylation or a copper-catalyzed coupling of methyl diazoacetate furnishing alkyne 14 and allene derivative 15. The Pauson-Khand reaction of the enyne 4c afforded a diastereomeric mixture of methyl 5-oxohexahydropentalen-2-carboxylate 16 in moderate yield.