(7aR,11aS)-1,2,3,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinoline-5-thione | 1108206-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (7aR,11aS)-1,2,3,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinoline-5-thione
• CAS: 1108206-56-9
• 化学式: C₁₂H₁₉NS
• 分子量: 209.356
• InChiKey: FAULLKSNVMSYDM-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (7aR,11aS)-1,2,3,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinoline-5-thione 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 0.5h， 以80%的产率得到
  参考文献：
  名称：

  A Concise, metathesis based approach to construction of the lepadiformine/cylindricine tricyclic framework

  摘要：

  A tandem dienyne metathesis based strategy has been developed for construction of the core tricyclic framework found in the lepadiformine and cylindricine alkaloids. 2-Pentenyl-2-ethynylpyrollidine acrylamide that serves as the starting material for the key ruthenium carbene catalyzed metathesis process is prepared by using a concise route starting with L-proline. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.027
• 作为产物：
  描述：

  (7aR,11aS)-1,2,3,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinolin-5-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以96%的产率得到(7aR,11aS)-1,2,3,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinoline-5-thione
  参考文献：
  名称：

  Prolinamide/PPTS-Catalyzed Hajos-Parrish Annulation: Efficient Approach to the Tricyclic Core of Cylindricine-Type Alkaloids

  摘要：

  一系列带有高度官能团化取代基的维兰德-米舍酮类似物，通过使用催化量的脯氨酰胺和PPTS，在高对映选择性和良好产率下被高效构建。我们成功地利用这一反应作为关键步骤，合成了环柱碱类生物碱的三环核心结构。

  DOI：

  10.1055/s-0028-1083542

文献信息

• Prolinamide/PPTS-Catalyzed Hajos-Parrish Annulation: Efficient Approach to the Tricyclic Core of Cylindricine-Type Alkaloids
  作者：Yong-Qiang Tu、Fu-Min Zhang、Xiao-Ming Zhang、Min Wang、Chun-An Fan、Yi-Jun Jiang、Shu-Yu Zhang

  DOI：10.1055/s-0028-1083542

  日期：——

  A series of Wieland-Miescher ketone analogues bearing highly functionalized substituents are efficiently constructed in high enantioselectivities and good yields using catalytic amounts of prolinamide and PPTS. We have successfully utilized this reaction as a key step to synthesize the tricyclic core of cylindricine type alkaloids.

  一系列带有高度官能团化取代基的维兰德-米舍酮类似物，通过使用催化量的脯氨酰胺和PPTS，在高对映选择性和良好产率下被高效构建。我们成功地利用这一反应作为关键步骤，合成了环柱碱类生物碱的三环核心结构。
• A Concise, metathesis based approach to construction of the lepadiformine/cylindricine tricyclic framework
  作者：Jiwen Zou、Dae Won Cho、Patrick S. Mariano

  DOI：10.1016/j.tet.2010.06.027

  日期：2010.8

  A tandem dienyne metathesis based strategy has been developed for construction of the core tricyclic framework found in the lepadiformine and cylindricine alkaloids. 2-Pentenyl-2-ethynylpyrollidine acrylamide that serves as the starting material for the key ruthenium carbene catalyzed metathesis process is prepared by using a concise route starting with L-proline. (c) 2010 Elsevier Ltd. All rights reserved.