3-Methyl-2-(2-methyl-2-nitrodecyl)cyclohex-2-en-1-one | 331811-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-2-(2-methyl-2-nitrodecyl)cyclohex-2-en-1-one
• CAS: 331811-99-5
• 化学式: C₁₈H₃₁NO₃
• 分子量: 309.449
• InChiKey: OOJCLMKAYSCIOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-octoxyphenyl)benzoyl chloride 、 3-Methyl-2-(2-methyl-2-nitrodecyl)cyclohex-2-en-1-one 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以27%的产率得到
  参考文献：
  名称：

  Synthesis of α,α'-Asymmetric Nitroxide Radicals by C- or O-Acylation of Radical-enolate Intermediates Generated by Reduction of Homoallylic Nitro Enones with Samarium(II) Iodide

  摘要：

  A new synthetic method to form two structurally different alpha, alpha'-asymmetric bicyclic nitroxides from the same substrate is described. Reduction of certain homoallylic nitro enones bearing a long alkyl chain with 3.0 equiv of SmI2 in THF at -78 degreesC gave a nitroxide radical-anion species of type A, while the same reduction followed by addition of HMPA at -78 degreesC resulted in the isomerization of the double bond to afford a different nitroxide radical anion species of type C. The former radical-anion undergoes O-acylation by the reaction with acyl chlorides to give alpha, alpha'-asymmetric bicyclic ester-nitroxides of type B, while the latter one does C-acylation to produce alpha, alpha'-asymmetric bicyclic beta -diketo nitroxides of type D.

  DOI：

  10.3987/com-00-s(i)19
• 作为产物：
  描述：

  2-Benzenesulfonylmethyl-3-methyl-cyclohex-2-enone 、 C₁₀H₂₀NO₂^(1-)*Li⁽¹⁺⁾ 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到3-Methyl-2-(2-methyl-2-nitrodecyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of α,α'-Asymmetric Nitroxide Radicals by C- or O-Acylation of Radical-enolate Intermediates Generated by Reduction of Homoallylic Nitro Enones with Samarium(II) Iodide

  摘要：

  A new synthetic method to form two structurally different alpha, alpha'-asymmetric bicyclic nitroxides from the same substrate is described. Reduction of certain homoallylic nitro enones bearing a long alkyl chain with 3.0 equiv of SmI2 in THF at -78 degreesC gave a nitroxide radical-anion species of type A, while the same reduction followed by addition of HMPA at -78 degreesC resulted in the isomerization of the double bond to afford a different nitroxide radical anion species of type C. The former radical-anion undergoes O-acylation by the reaction with acyl chlorides to give alpha, alpha'-asymmetric bicyclic ester-nitroxides of type B, while the latter one does C-acylation to produce alpha, alpha'-asymmetric bicyclic beta -diketo nitroxides of type D.

  DOI：

  10.3987/com-00-s(i)19

文献信息

• Synthesis of α,α'-Asymmetric Nitroxide Radicals by C- or O-Acylation of Radical-enolate Intermediates Generated by Reduction of Homoallylic Nitro Enones with Samarium(II) Iodide
  作者：Rui Tamura、Satoshi Shimono、Kasuke Fujita、Ken-ichi Hirao

  DOI：10.3987/com-00-s(i)19

  日期：——

  A new synthetic method to form two structurally different alpha, alpha'-asymmetric bicyclic nitroxides from the same substrate is described. Reduction of certain homoallylic nitro enones bearing a long alkyl chain with 3.0 equiv of SmI2 in THF at -78 degreesC gave a nitroxide radical-anion species of type A, while the same reduction followed by addition of HMPA at -78 degreesC resulted in the isomerization of the double bond to afford a different nitroxide radical anion species of type C. The former radical-anion undergoes O-acylation by the reaction with acyl chlorides to give alpha, alpha'-asymmetric bicyclic ester-nitroxides of type B, while the latter one does C-acylation to produce alpha, alpha'-asymmetric bicyclic beta -diketo nitroxides of type D.