2-cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate | 1439358-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate
• 英文别名: 2-Cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate；2-cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
• CAS: 1439358-81-2
• 化学式: C₂₆H₂₄N₂O₆
• 分子量: 460.486
• InChiKey: YRNQQTLBRZGAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到2-cyanoethyl 4a-bromo-2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylate
  参考文献：
  名称：

  Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines

  摘要：

  Polycyclic 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines having ester or cyano group at the position 3 of dihydropyridine ring have been synthesised. Reactivity of N-bromosuccinimide (NBS) towards polycyclic 1,4-dihydropyridine derivatives has been investigated. It has been found that 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides are easily oxidised with NBS in methanol at rt in high yields, whereas 4,5-dihydro-1H-indeno[1,2-b]pyridines in reaction with NBS in methanol are brominated at 4a position affording stable 4a-bromo-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylates or unstable 3-carbonitriles, which rapidly undergo dehydrobromination reaction leading to the corresponding 5H-indeno[1,2-b]pyridine-3-carbonitriles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.060
• 作为产物：
  描述：

  2-cyanoethyl 4a-bromo-2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.03h， 以85%的产率得到2-cyanoethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate
  参考文献：
  名称：

  Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines

  摘要：

  Polycyclic 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines having ester or cyano group at the position 3 of dihydropyridine ring have been synthesised. Reactivity of N-bromosuccinimide (NBS) towards polycyclic 1,4-dihydropyridine derivatives has been investigated. It has been found that 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides are easily oxidised with NBS in methanol at rt in high yields, whereas 4,5-dihydro-1H-indeno[1,2-b]pyridines in reaction with NBS in methanol are brominated at 4a position affording stable 4a-bromo-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylates or unstable 3-carbonitriles, which rapidly undergo dehydrobromination reaction leading to the corresponding 5H-indeno[1,2-b]pyridine-3-carbonitriles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.060

文献信息

• Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines
  作者：Brigita Cekavicus、Brigita Vigante、Martins Rucins、Kintija Birkmane、Marina Petrova、Sergey Belyakov、Liga Zuka、Aiva Plotniece、Karlis Pajuste、Marina Gosteva、Arkadij Sobolev

  DOI：10.1016/j.tet.2013.04.060

  日期：2013.7

  Polycyclic 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines having ester or cyano group at the position 3 of dihydropyridine ring have been synthesised. Reactivity of N-bromosuccinimide (NBS) towards polycyclic 1,4-dihydropyridine derivatives has been investigated. It has been found that 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides are easily oxidised with NBS in methanol at rt in high yields, whereas 4,5-dihydro-1H-indeno[1,2-b]pyridines in reaction with NBS in methanol are brominated at 4a position affording stable 4a-bromo-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylates or unstable 3-carbonitriles, which rapidly undergo dehydrobromination reaction leading to the corresponding 5H-indeno[1,2-b]pyridine-3-carbonitriles. (C) 2013 Elsevier Ltd. All rights reserved.