(S)-2-[2-(2,6-Dimethoxy-cyclohexa-2,5-dienyl)-ethyl]-piperidine | 856015-27-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-2-[2-(2,6-Dimethoxy-cyclohexa-2,5-dienyl)-ethyl]-piperidine
• CAS: 856015-27-5
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: TVPADLIRESKYRX-LBPRGKRZSA-N

物化性质

• 沸点：
  393.3±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-(2,6-Dimethoxy-cyclohexa-2,5-dienyl)-ethyl]-piperidine 在 盐酸 作用下， 反应 0.5h， 以54%的产率得到(S)-1,2,3,4,4a,5,6,8,9,10-Decahydro-pyrido[1,2-a]quinolin-7-one
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s
• 作为产物：
  描述：

  (S)-(-)-2-哌啶乙醇 在 氨 、 氢溴酸 、 potassium amide 作用下， 反应 7.33h， 生成 (S)-2-[2-(2,6-Dimethoxy-cyclohexa-2,5-dienyl)-ethyl]-piperidine
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s