(S)-diethyl 5-bromo-1-methyl-2-oxo-4',9'-dihydrospiro[indoline-3,1'-pyrido[3,4-b]indole]-3',3'(2'H)-dicarboxylate | 1340563-79-2

• 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)-diethyl 5-bromo-1-methyl-2-oxo-4',9'-dihydrospiro[indoline-3,1'-pyrido[3,4-b]indole]-3',3'(2'H)-dicarboxylate
• 英文别名: diethyl (1S)-5'-bromo-1'-methyl-2'-oxospiro[4,9-dihydro-2H-pyrido[3,4-b]indole-1,3'-indole]-3,3-dicarboxylate
• CAS: 1340563-79-2
• 化学式: C₂₅H₂₄BrN₃O₅
• 分子量: 526.387
• InChiKey: GLOQTHNWKSACLI-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氯-1-甲基-1H-吲哚-2,3-二酮 、 在 (S)-(+)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-diethyl 5-bromo-1-methyl-2-oxo-4',9'-dihydrospiro[indoline-3,1'-pyrido[3,4-b]indole]-3',3'(2'H)-dicarboxylate 、 (S)-diethyl 5-bromo-1-methyl-2-oxo-4',9'-dihydrospiro[indoline-3,1'-pyrido[3,4-b]indole]-3',3'(2'H)-dicarboxylate
  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