(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.