Ethyl 5-bromo-2-(2-cyano-4-methyl-3-oxocyclohexyl)pentanoate | 1398120-22-3

• 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: Ethyl 5-bromo-2-(2-cyano-4-methyl-3-oxocyclohexyl)pentanoate
• CAS: 1398120-22-3
• 化学式: C₁₅H₂₂BrNO₃
• 分子量: 344.249
• InChiKey: XBVQZZFFZDMSEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 5-bromo-2-(2-cyano-4-methyl-3-oxocyclohexyl)pentanoate 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 ethyl (1S,4aS,6S,8aR)-4a-cyano-6-methyl-5-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylate 、 ethyl (1R,4aS,6S,8aR)-4a-cyano-6-methyl-5-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  K2CO3/NaI-Induced Cyclization of ω-Bromo α-Cyano Ketones: A New Annulation Approach for the Formation of Carbalkoxycyclohexane Ring System

  摘要：

  An operationally simple and highly effective annulation process, making use of ZnCl2-catalyzed Michael addition and K2CO3/NaI-induced cyclization as key manipulations, has been developed to construct various bicyclic systems with a high level of functionalization valuable for further synthetic elaboration.

  DOI：

  10.1055/s-0031-1290386
• 作为产物：
  描述：

  5-Methyl-6-oxocyclohexene-1-carbonitrile 、 在 zinc(II) chloride 作用下， 反应 1.0h， 以85%的产率得到Ethyl 5-bromo-2-(2-cyano-4-methyl-3-oxocyclohexyl)pentanoate
  参考文献：
  名称：

  K2CO3/NaI-Induced Cyclization of ω-Bromo α-Cyano Ketones: A New Annulation Approach for the Formation of Carbalkoxycyclohexane Ring System

  摘要：

  An operationally simple and highly effective annulation process, making use of ZnCl2-catalyzed Michael addition and K2CO3/NaI-induced cyclization as key manipulations, has been developed to construct various bicyclic systems with a high level of functionalization valuable for further synthetic elaboration.

  DOI：

  10.1055/s-0031-1290386