(2R,6S,E)-1-but-3-enoyl-2-(3,4-dimethoxyphenyl)-6-styrylpiperidin-4-one | 1139874-41-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2R,6S,E)-1-but-3-enoyl-2-(3,4-dimethoxyphenyl)-6-styrylpiperidin-4-one
• 英文别名: (2R,6S)-1-but-3-enoyl-2-(3,4-dimethoxyphenyl)-6-[(E)-2-phenylethenyl]piperidin-4-one
• CAS: 1139874-41-1
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: XLIHUHUXIXCVMY-UEUVIKQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (2R,6S,E)-1-but-3-enoyl-2-(3,4-dimethoxyphenyl)-6-styrylpiperidin-4-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(4R,9aS)-4-(3,4-dimethoxyphenyl)-3,4-dihydro-1H-quinolizine-2,6(7H,9aH)-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
• 作为产物：
  描述：

  乙烯基乙酸 、 (2R,6S)-2-(3,4-dimethoxyphenyl)-6-[(E)-2-phenylethenyl]piperidin-4-one 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以2.43 g的产率得到(2R,6S,E)-1-but-3-enoyl-2-(3,4-dimethoxyphenyl)-6-styrylpiperidin-4-one
  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.