(11bR)-11b-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one | 959979-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (11bR)-11b-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
• 英文别名: (R)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one；11b-methyl-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indol-3-one；(11bR)-11b-methyl-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 959979-01-2
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: YZCPZTYKWQSAJI-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methylpyrrolidin-2-one 在 R,R-derivative of cyclohexyl-carbamothioyl-L-valinamide 三甲基氯硅烷 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以92%的产率得到(11bR)-11b-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
  参考文献：
  名称：

  羟基内酰胺的对映选择性 Pictet-Spengler 型环化：阴离子结合的 H 键供体催化

  摘要：

  在硫脲催化的色胺衍生的羟基内酰胺的环化中获得高度对映体富集的吲哚嗪酮和喹嗪酮产物。取代基和反离子效应研究指出了一种新的催化机制，涉及限速阴离子提取和硫脲结合。

  DOI：

  10.1021/ja076179w

文献信息

• Ring-Closing Metathesis/Isomerization/Pictet–Spengler Cascade <i>via</i> Ruthenium/Chiral Phosphoric Acid Sequential Catalysis
  作者：Quan Cai、Xiao-Wei Liang、Shou-Guo Wang、Jun-Wei Zhang、Xiao Zhang、Shu-Li You

  DOI：10.1021/ol302215u

  日期：2012.10.5

  with Hoveyda–Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-β-carbolines (up to 98% yield, 99% ee) through a ring-closing metathesis/isomerization/Pictet–Spengler cascade reaction via sequential catalysis.

  手性磷酸与Hoveyda-Grubbs II催化剂共同作用，通过闭环易位/异构化/ Pictet-Spengler级联反应（通过顺序催化）实现了对映体富集的四氢-β-咔啉的高效合成（产率高达98％，ee为99％）。。
• Enantioselective Brønsted Acid-Catalyzed <i>N</i>-Acyliminium Cyclization Cascades
  作者：Michael E. Muratore、Chloe A. Holloway、Adam W. Pilling、R. Ian Storer、Graham Trevitt、Darren J. Dixon

  DOI：10.1021/ja9024885

  日期：2009.8.12

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.
• Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams:  H-Bond Donor Catalysis by Anion Binding
  作者：Izzat T. Raheem、Parvinder S. Thiara、Emily A. Peterson、Eric N. Jacobsen

  DOI：10.1021/ja076179w

  日期：2007.11.1

  indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.

  在硫脲催化的色胺衍生的羟基内酰胺的环化中获得高度对映体富集的吲哚嗪酮和喹嗪酮产物。取代基和反离子效应研究指出了一种新的催化机制，涉及限速阴离子提取和硫脲结合。