4-[11-tosyl-1-vinyl-6,11-dihydro-3H,5H-indolizino[8,7-b]indol-11b-yl]-but-3-en-2-one | 1068441-81-5

• 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: 4-[11-tosyl-1-vinyl-6,11-dihydro-3H,5H-indolizino[8,7-b]indol-11b-yl]-but-3-en-2-one
• 英文别名: (E)-4-[1-ethenyl-11-(4-methylphenyl)sulfonyl-5,6-dihydro-3H-indolizino[8,7-b]indol-11b-yl]but-3-en-2-one
• CAS: 1068441-81-5
• 化学式: C₂₇H₂₆N₂O₃S
• 分子量: 458.581
• InChiKey: MJKMAAAYFZMTOY-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  11-(tolylsulfonyl)-1-vinyl-5,6,11,11b-tetrahydro-3H-indolizino[8,7-b]indole 、 3-丁炔-2-酮 以 二氯甲烷 为溶剂， 反应 24.0h， 以53%的产率得到4-[11-tosyl-1-vinyl-6,11-dihydro-3H,5H-indolizino[8,7-b]indol-11b-yl]-but-3-en-2-one
  参考文献：
  名称：

  Novel domino reactions in β-carbolines with triple bonded dienophiles

  摘要：

  Vinylpyrrolo-[2,1-a]-beta-carbolines 1 give different products upon reaction with dienophiles. With dimethyl acetylenedicarboxylate (DMAD), a novel domino process takes place, involving Michael attack and rearrangement, affording complex polycycles like 3, 4, and S. Diels-Alder cycloadditions are favored in the presence of Lewis acids and are the only reactions with dimethyl maleate. When 3-butyn-2-one is used as dienophile, a Stevens rearrangement is observed giving product 9. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.025

文献信息

• Novel domino reactions in β-carbolines with triple bonded dienophiles
  作者：Álvaro González-Gómez、Gema Domínguez、Ulises Amador、Javier Pérez-Castells

  DOI：10.1016/j.tetlet.2008.07.025

  日期：2008.9

  Vinylpyrrolo-[2,1-a]-beta-carbolines 1 give different products upon reaction with dienophiles. With dimethyl acetylenedicarboxylate (DMAD), a novel domino process takes place, involving Michael attack and rearrangement, affording complex polycycles like 3, 4, and S. Diels-Alder cycloadditions are favored in the presence of Lewis acids and are the only reactions with dimethyl maleate. When 3-butyn-2-one is used as dienophile, a Stevens rearrangement is observed giving product 9. (C) 2008 Elsevier Ltd. All rights reserved.