1-allyl-2,9-dipropargyl-2,3,4,9-tetrahydro-1H-β-carboline | 1156537-60-8

• 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: 1-allyl-2,9-dipropargyl-2,3,4,9-tetrahydro-1H-β-carboline
• CAS: 1156537-60-8
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: SGQFMQYCZFNBSI-UHFFFAOYSA-N

物化性质

• 沸点：
  431.3±45.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  8.17
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-allyl-2,9-dipropargyl-2,3,4,9-tetrahydro-1H-β-carboline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以55%的产率得到N-(2-{2-[buta-1,3-dien-1-yl]-1-propargyl-1H-indol-3-yl}ethyl)-N-hydroxyprop-2-yn-1-amine
  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-propargyl-N-[2-(1-propargyl-1H-indol-3-yl)ethyl]formamide 、 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64%的产率得到1-allyl-2,9-dipropargyl-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