methyl 2-(cyanomethyl)-6-methyl-3-oxo-6-heptenoate | 137393-41-0

• 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)-6-methyl-3-oxo-6-heptenoate
• 英文别名: Methyl 2-(cyanomethyl)-6-methyl-3-oxohept-6-enoate
• CAS: 137393-41-0
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: OYSMXPQKEUFYPD-UHFFFAOYSA-N

物化性质

• 沸点：
  343.4±37.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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)-6-methyl-3-oxo-6-heptenoate 在 manganese triacetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以51%的产率得到methyl 5-methyl-2,6-dioxobicyclo<3.2.1>octane-1-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 6-methyl-3-oxo-6-heptenoate 、 溴乙腈 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以65%的产率得到methyl 2-(cyanomethyl)-6-methyl-3-oxo-6-heptenoate
  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

文献信息

• Termination of manganese(III)-based oxidative free-radical cyclizations by addition to nitriles. Formation of cyclopentanones and cyclohexanones
  作者：Barry B. Snider、Brad O. Buckman

  DOI：10.1021/jo00027a056

  日期：1992.1

  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.