tert-butyl 9-allyl-1-ethynyl-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylate | 1156537-82-4

• 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: tert-butyl 9-allyl-1-ethynyl-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylate
• CAS: 1156537-82-4
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: AXLFVSLWBDCKEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  9-allyl-1-ethynyl-2,3,4,9-tetrahydro-1H-β-carboline 、 二碳酸二叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以60%的产率得到tert-butyl 9-allyl-1-ethynyl-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylate
  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