8-methyl-7-(thiophen-2-yl)-9,11-dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-one | 1585942-35-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-methyl-7-(thiophen-2-yl)-9,11-dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-one
• 英文别名: 13-Methyl-11-thiophen-2-yl-8-oxa-14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,12,15-hexaen-9-one；13-methyl-11-thiophen-2-yl-8-oxa-14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,12,15-hexaen-9-one
• CAS: 1585942-35-3
• 化学式: C₁₈H₁₃N₃O₂S
• 分子量: 335.386
• InChiKey: GWHIJRRALWWZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 4-羟基香豆素 、 3-氨基-5-甲基吡唑 在 tetra-N-butylammonium tribromide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以78%的产率得到8-methyl-7-(thiophen-2-yl)-9,11-dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-one
  参考文献：
  名称：

  Synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones involving one-pot three-component tandem Knoevenagel–Michael reaction catalyzed by n-tetrabutylammonium tribromide (TBATB)

  摘要：

  The synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones was achieved through one-pot three-component reaction from 4-hydroxycoumarin, aldehydes, and 3-amino-5-methyl-pyrazole in acetonitrile using 5 mol % TBATB as the catalyst under reflux condition. The product formation is through tandem Knoevenagel-Michael reaction followed by concomitant cyclization. Simple reaction procedure, shorter reaction time, good yields, avoidance of aqueous work-up, and column chromatographic separation are some of the salient features of the present protocol. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.014

文献信息

• Synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones involving one-pot three-component tandem Knoevenagel–Michael reaction catalyzed by n-tetrabutylammonium tribromide (TBATB)
  作者：Arindam Ghosh、Abu T. Khan

  DOI：10.1016/j.tetlet.2014.02.014

  日期：2014.3

  The synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones was achieved through one-pot three-component reaction from 4-hydroxycoumarin, aldehydes, and 3-amino-5-methyl-pyrazole in acetonitrile using 5 mol % TBATB as the catalyst under reflux condition. The product formation is through tandem Knoevenagel-Michael reaction followed by concomitant cyclization. Simple reaction procedure, shorter reaction time, good yields, avoidance of aqueous work-up, and column chromatographic separation are some of the salient features of the present protocol. (c) 2014 Elsevier Ltd. All rights reserved.