(S)-6'-methoxy-1-(4-methoxybenzyl)-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one | 1340563-56-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (S)-6'-methoxy-1-(4-methoxybenzyl)-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one
• 英文别名: (1S)-6-methoxy-1'-[(4-methoxyphenyl)methyl]spiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,3'-indole]-2'-one
• CAS: 1340563-56-5
• 化学式: C₂₇H₂₅N₃O₃
• 分子量: 439.514
• InChiKey: IQESWHSBLMJCQE-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基色胺 、 1-(4-甲氧基-苄基)-1H-吲哚-2,3-二酮 在 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-6'-methoxy-1-(4-methoxybenzyl)-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one 、 (R)-6'-methoxy-1-(4-methoxyphenyl)-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one
  参考文献：
  名称：

  Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones

  摘要：

  The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-beta-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.071

文献信息

• Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
  作者：Joseph J. Badillo、Abel Silva-García、Benjamin H. Shupe、James C. Fettinger、Annaliese K. Franz

  DOI：10.1016/j.tetlet.2011.08.071

  日期：2011.10

  The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-beta-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration. (C) 2011 Elsevier Ltd. All rights reserved.