(4S,9aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H-quinolizine-2,6(7H,8H)-dione | 1139874-48-8

• 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: (4S,9aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H-quinolizine-2,6(7H,8H)-dione
• 英文别名: (4S,9aS)-4-(3,4-dimethoxyphenyl)-3,4,7,8,9,9a-hexahydro-1H-quinolizine-2,6-dione
• CAS: 1139874-48-8
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: METMXDMHQRWSIO-JSGCOSHPSA-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：

  (4S,9aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H-quinolizine-2,6(7H,8H)-dione 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.17h， 生成 (2R,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine
  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：

  (4S,9aR)-4-(3,4-dimethoxyphenyl)-3,4-dihydro-1H-quinolizine-2,6(7H,9aH)-dione 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (4S,9aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H-quinolizine-2,6(7H,8H)-dione
  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

文献信息

• 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.