ethyl 1-benzyl-2-oxo-1,3,4,5,6,7-hexahydro-4a(2H)-quinolinecarboxylate | 154819-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 1-benzyl-2-oxo-1,3,4,5,6,7-hexahydro-4a(2H)-quinolinecarboxylate
• 英文别名: ethyl 1-benzyl-2-oxo-4,5,6,7-tetrahydro-3H-quinoline-4a-carboxylate
• CAS: 154819-92-8
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: MBDOTLCQAGORQF-UHFFFAOYSA-N

物化性质

• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-2-oxo-1,3,4,5,6,7-hexahydro-4a(2H)-quinolinecarboxylate 在 盐酸 、 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-benzyl-3,4,5,6,7,8-hexahydro-2(1H)-quinolinone
  参考文献：
  名称：

  甲基甘卡尼丁的[6-6-6] ABE三环类似物的合成

  摘要：

  利用β-烯氨基酮的有效氮杂环化，然后轻松脱羧形成BE环，已经开发了具有C-1氧化取代基的甲基甘可碱碱桥接[6-6-6] ABE三环类似物的新合成物。随后的形成A环的过程是通过环戊基酰基自由基环化以及关键的C-1氧官能团的随附设备完成的。

  DOI：

  10.1016/j.cclet.2021.03.068
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 ethyl 1-benzyl-2-oxo-1,3,4,5,6,7-hexahydro-4a(2H)-quinolinecarboxylate
  参考文献：
  名称：

  Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine

  摘要：

  N-alkylenamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles. In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product. A variety of functional groups, which include -COMe, -COPh, -CO(2)R, -CONHPh, -CN, -P(O)(OEt)(2), and -SO(2)Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process. When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the ate-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity. The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.

  DOI：

  10.1021/jo00086a009

文献信息

• Synthesis of [6-6-6] ABE tricyclic ring analogues of methyllycaconitine
  作者：Dan Xiao、Xin Zhao、Jiang Lei、Mengqian Zhu、Liang Xu

  DOI：10.1016/j.cclet.2021.03.068

  日期：2021.10

  A new synthesis of the bridged [6-6-6] ABE tricyclic ring analogues of methyllycaconitine with the C-1 oxygenated substituents has been developed using an efficient aza-annulation of β-enamino ketone followed by a facile decarboxylation to form BE rings. Subsequent elaboration to form the A ring was achieved by a transannular acyl radical cyclization with concomitant equipment of the key C-1 oxygen

  利用β-烯氨基酮的有效氮杂环化，然后轻松脱羧形成BE环，已经开发了具有C-1氧化取代基的甲基甘可碱碱桥接[6-6-6] ABE三环类似物的新合成物。随后的形成A环的过程是通过环戊基酰基自由基环化以及关键的C-1氧官能团的随附设备完成的。
• Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00086a009

  日期：1994.4

  N-alkylenamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles. In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product. A variety of functional groups, which include -COMe, -COPh, -CO(2)R, -CONHPh, -CN, -P(O)(OEt)(2), and -SO(2)Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process. When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the ate-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity. The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.