1-allyl-2-propargyl-9-tosyl-2,3,4,9-tetrahydro-1H-β-carboline | 1156537-58-4

• 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: 1-allyl-2-propargyl-9-tosyl-2,3,4,9-tetrahydro-1H-β-carboline
• CAS: 1156537-58-4
• 化学式: C₂₄H₂₄N₂O₂S
• 分子量: 404.533
• InChiKey: CJDNZKWVPFVTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.31
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-allyl-2-propargyl-9-tosyl-2,3,4,9-tetrahydro-1H-β-carboline 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以44%的产率得到12-tosyl-3-vinyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine
  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-(1-tosyl-1H-indol-3-yl)ethyl]-N-propargylformamide 、 烯丙基溴化镁 在 三氯氧磷 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 18.0h， 以51%的产率得到1-allyl-2-propargyl-9-tosyl-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