2-allyl-1-ethynyl-9-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline | 868846-96-2

• 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: 2-allyl-1-ethynyl-9-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 2-allyl-1-ethynyl-9-tosyl-2,3,4,9-tetrahydro-1H-β-carboline；1-ethynyl-9-(4-methylphenyl)sulfonyl-2-prop-2-enyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 868846-96-2
• 化学式: C₂₃H₂₂N₂O₂S
• 分子量: 390.506
• InChiKey: ASJRWTOUAZEJST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-1-ethynyl-9-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以35%的产率得到11-(tolylsulfonyl)-1-vinyl-6,11-dihydro-5H-indolizino[8,7-b]indole
  参考文献：
  名称：

  Novel chemistry of β-carbolines. Expedient synthesis of polycyclic scaffolds

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.02.051
• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]甲酰胺 在 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 2-allyl-1-ethynyl-9-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Enyne and dienyne metathesis reactions in β-carbolines

  摘要：

  New indolic enynes and dienynes, based on the P-carboline system, give metathesis products with ruthenium catalysts. The synthesis of the starting materials is readily achieved from tryptamine. The tuning up of the conditions for the metathesis is discussed. Cascade metathesis gives an oxidized pentacyclic product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.140

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.