dimethyl 1-isopropenyl-11-tosyl-1-vinyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indole-2,3-dicarboxylate | 1068441-75-7

• 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: dimethyl 1-isopropenyl-11-tosyl-1-vinyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indole-2,3-dicarboxylate
• 英文别名: dimethyl 1-ethenyl-11-(4-methylphenyl)sulfonyl-1-prop-1-en-2-yl-6,11b-dihydro-5H-indolizino[8,7-b]indole-2,3-dicarboxylate
• CAS: 1068441-75-7
• 化学式: C₃₀H₃₀N₂O₆S
• 分子量: 546.644
• InChiKey: YIGQICVKNXUETK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-isopropenyl-11-(tolylsulfonyl)-5,6,11,11b-tetrahydro-3H-indolizino[8,7-b]indole 、 丁炔二酸二甲酯 以 二氯甲烷 为溶剂， 反应 48.0h， 以52%的产率得到dimethyl (9E,11Z)-8-tosyl-11-isopropenyl-8,14-diazatetracyclo[12,2,2,0^1,9,0^2,7]octadeca-2,4,6,9,11,15-hexaene-15,16-dicarboxylate
  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 chemistry of β-carbolines. Expedient synthesis of polycyclic scaffolds
  作者：Álvaro González-Gómez、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1016/j.tet.2009.02.051

  日期：2009.4

  Functionalization of beta-carbolines is a challenge as numerous natural alkaloids with different biological activities present this heterocycle. The RCM is used herein with allyl-, vinyl-, ethynyl-, and propargyl-beta-carbolines to generate additionally fused hetero- and carbocycles, and it is combined with other cyclization processes to achieve great molecular complexity in one synthetic step. Thus, an RCM-Diels-Alder sequence gives pentacyclic Compounds related with certain alkaloids. On the other hand, vinyl-pyrrolo[2,1-a]-beta-carbolines and vinyl-beta-carbolines give different products upon reaction with activated dienophiles. Thus, a novel domino processes affords complex polycycles like 35-38. Other alkynes like 3-butyn-2-one give a Stevens rearrangement. (C) 2009 Elsevier Ltd. All rights reserved.