2-allyl-9-tosyl-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline | 1068441-76-8

• 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-9-tosyl-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-ethenyl-9-(4-methylphenyl)sulfonyl-2-prop-2-enyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 1068441-76-8
• 化学式: C₂₃H₂₄N₂O₂S
• 分子量: 392.522
• InChiKey: VHGHFOXKMJVHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 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-9-tosyl-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline 在 gold(III) chloride 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 dimethyl 2-(allyl(2-(2-((E)-5-methoxy-5-oxopent-1-enyl)-1-tosyl-1H-indol-3-yl)ethyl)amino)maleate
  参考文献：
  名称：

  Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines

  摘要：

  2 烯丙基-1-乙烯基-δ-羰基化合物和二氢吡咯-δ-羰基化合物通过新型重排反应与活化的内炔发生反应，生成复杂的多环结构。有利的反应途径取决于反应条件和金催化剂的存在。特别是在与 2 等量的炔烃反应时，会形成新的六环结构 10，并具有完全的立体控制能力。

  DOI：

  10.1039/c2ob25755f
• 作为产物：
  描述：

  N-allyl-N-[2-(1-tolylsulfonyl-1H-indol-3-yl)-ethyl]-formamide 、 乙烯基溴化镁 在 三氯氧磷 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 34.0h， 以93%的产率得到2-allyl-9-tosyl-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline
  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

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.