methyl 3-methylpent-5-ynecarboxylate

• 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-methylpent-5-ynecarboxylate
• 英文别名: Methyl 3-methylpent-4-ynoate；methyl 3-methylpent-4-ynoate
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: NEEUKEIOMPYPCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-methylpent-5-ynecarboxylate 、 苄基叠氮 在 copper(l) iodide 、 triphenethylamine 、 三乙胺 作用下， 以 乙腈 为溶剂， 以72%的产率得到methyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-3-butanoate
  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
• 作为产物：
  描述：

  Methyl (Z)-3-methyl-5-tributylstannylpent-4-enoate 在 lead(IV) acetate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以85%的产率得到methyl 3-methylpent-5-ynecarboxylate
  参考文献：
  名称：

  Barbero, Asuncion; Cuadrado, Purificacion; Fleming, Ian, Journal of the Chemical Society. Perkin transactions I, 1993, # 14, p. 1657 - 1662

  摘要：

  DOI：

文献信息

• 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.
• Barbero, Asuncion; Cuadrado, Purificacion; Fleming, Ian, Journal of the Chemical Society. Perkin transactions I, 1993, # 14, p. 1657 - 1662
  作者：Barbero, Asuncion、Cuadrado, Purificacion、Fleming, Ian、Gonzalez, Ana M.、Pulido, Francisco J.、Rubio, Rosa

  DOI：——

  日期：——