(4R,9aR)-4-(3,4-Dimethoxy-phenyl)-hexahydro-quinolizine-2,6-dione

• 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: (4R,9aR)-4-(3,4-Dimethoxy-phenyl)-hexahydro-quinolizine-2,6-dione
• 英文别名: (4R,9aR)-4-(3,4-dimethoxyphenyl)-3,4,7,8,9,9a-hexahydro-1H-quinolizine-2,6-dione
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: METMXDMHQRWSIO-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,9aR)-4-(3,4-Dimethoxy-phenyl)-hexahydro-quinolizine-2,6-dione 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.17h， 以92%的产率得到4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizin-2-ol
  参考文献：
  名称：

  An Enantioselective Organocatalytic Approach to Both Enantiomers of Lasubine II

  摘要：

  A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps.

  DOI：

  10.1021/jo900141f
• 作为产物：
  描述：

  1-[1-(3,4-Dimethoxy-phenyl)-3-trimethylsilanylmethyl-but-3-enyl]-6-hydroxy-piperidin-2-one 在 臭氧 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.03h， 生成 (4R,9aR)-4-(3,4-Dimethoxy-phenyl)-hexahydro-quinolizine-2,6-dione
  参考文献：
  名称：

  A Synthesis of the Quinolizidine Alkaloids (±)-Lasubine I and (±)-Lasubine II

  摘要：

  DOI：

  10.3987/com-97-8073

文献信息

• Vinylogous Mukaiyama–Michael Reactions of Dihydropyridinones
  作者：Hui Li、Jimmy Wu

  DOI：10.1021/acs.orglett.5b02778

  日期：2015.11.6

  An In(III)-catalyzed vinylogous addition of O-silyl vinylketene acetals to 2,3-dihydro-4-pyridinones has been developed. The method features the unprecedented employment of supersilyl groups to influence the gamma versus alpha regiochemical control of vinylogous Mukaiyama Michael (vM-Michael) reactions when gamma-substituted O-silyl vinylketene acetals are used. We also demonstrate that these reactions allow facile access to quinolizidine-based alkaloids such as deoxynupharidine and well as lasubine I and II.
• An Enantioselective Organocatalytic Approach to Both Enantiomers of Lasubine II
  作者：Jorge M. M. Verkade、Ferdi van der Pijl、Marian M. J. H. P. Willems、Peter J. L. M. Quaedflieg、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo900141f

  日期：2009.4.17

  A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps.
• A Synthesis of the Quinolizidine Alkaloids (±)-Lasubine I and (±)-Lasubine II
  作者：Roland Remuson、Valérie Bardot、Daniel Gardette、Yvonne Gelas-Mialhe、Jean-Claude Gramain

  DOI：10.3987/com-97-8073

  日期：——