methyl 2-(2-cyanoethyl)-3-oxo-7(Z)-decenoate | 137393-46-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2-(2-cyanoethyl)-3-oxo-7(Z)-decenoate
• 英文别名: methyl (Z)-2-(2-cyanoethyl)-3-oxodec-7-enoate
• CAS: 137393-46-5
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: CDGKOCHYDOQTFB-PLNGDYQASA-N

物化性质

• 沸点：
  393.2±42.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  methyl 2-(2-cyanoethyl)-3-oxo-7(Z)-decenoate 在 manganese triacetate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 methyl (1α,6α)-1-(2-cyanoethyl)-2-oxo-6-propylcyclohexane-1-carboxylate 、 methyl (1α,4aβ,8aα)-1-ethyloctahydro-2,5-dioxo-4a(2H)-naphthalenecarboxylate
  参考文献：
  名称：

  Termination of manganese(III)-based oxidative free-radical cyclizations by addition to nitriles. Formation of cyclopentanones and cyclohexanones

  摘要：

  Mn(III)-based oxidative free-radical tandem cyclizations and annulations can be terminated by addition to nitriles. Cyclopentanones 20a (51%), 24a (57%), and 32a (54%) are formed in good yield. Annulation to give cyclohexanone 32b (41%) proceeds in moderate yield, although 20b (8%) and 24b (13%) are formed in poor yield in tandem cyclizations. Pyridine 39 (15%) is formed in ethanol by condensation of the enamine tautomer 37 of imine 31a with the oxidation byproduct 33a produced from radical 29a.

  DOI：

  10.1021/jo00027a056
• 作为产物：
  描述：

  methyl 3-oxo-7Z-decenoate 、 丙烯腈 在 甲醇 、 sodium 作用下， 反应 18.0h， 以20%的产率得到methyl 2-(2-cyanoethyl)-3-oxo-7(Z)-decenoate
  参考文献：
  名称：

  Termination of manganese(III)-based oxidative free-radical cyclizations by addition to nitriles. Formation of cyclopentanones and cyclohexanones

  摘要：

  Mn(III)-based oxidative free-radical tandem cyclizations and annulations can be terminated by addition to nitriles. Cyclopentanones 20a (51%), 24a (57%), and 32a (54%) are formed in good yield. Annulation to give cyclohexanone 32b (41%) proceeds in moderate yield, although 20b (8%) and 24b (13%) are formed in poor yield in tandem cyclizations. Pyridine 39 (15%) is formed in ethanol by condensation of the enamine tautomer 37 of imine 31a with the oxidation byproduct 33a produced from radical 29a.

  DOI：

  10.1021/jo00027a056