methyl 2-(cyanomethyl)-3-oxo-7(Z)-decenoate | 137393-45-4

• 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-(cyanomethyl)-3-oxo-7(Z)-decenoate
• 英文别名: methyl (Z)-2-(cyanomethyl)-3-oxodec-7-enoate
• CAS: 137393-45-4
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: GGHMJRYNOADZME-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-(cyanomethyl)-3-oxo-7(Z)-decenoate 在 manganese triacetate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 21.0h， 以57%的产率得到methyl (1α,3aβ,7aα)-1-ethyl-2,4-dioxooctahydro-3aH-indene-3a-carboxylate
  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 、 溴乙腈 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以56%的产率得到methyl 2-(cyanomethyl)-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