dimethyl 2-(6-bromo-2,6-dimethylhept-4-yn-3-yl)propanedioate | 1042163-47-2

• 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: dimethyl 2-(6-bromo-2,6-dimethylhept-4-yn-3-yl)propanedioate
• CAS: 1042163-47-2
• 化学式: C₁₄H₂₁BrO₄
• 分子量: 333.222
• InChiKey: FGACVTNSIVZHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(6-bromo-2,6-dimethylhept-4-yn-3-yl)propanedioate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以91%的产率得到dimethyl 2-isopropyl-3-(2-methylprop-1-enylidene)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a
• 作为产物：
  描述：

  dimethyl 2-(6-hydroxy-2,6-dimethylhept-4-yn-3-yl)propanedioate 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 28.0h， 以60%的产率得到dimethyl 2-(6-bromo-2,6-dimethylhept-4-yn-3-yl)propanedioate
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a