3-ethoxycarbonyl-2-methyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxide | 664973-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethoxycarbonyl-2-methyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxide
• 英文别名: Ethyl 2-methyl-5,5-dioxo-4-(3,4,5-trimethoxyphenyl)-1,4-dihydro-[1]benzothiolo[3,2-b]pyridine-3-carboxylate
• CAS: 664973-59-5
• 化学式: C₂₄H₂₅NO₇S
• 分子量: 471.531
• InChiKey: FQOQXWZQYMXIQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-2-methyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到3-ethoxycarbonyl-2-methyl-4-(3,4,5-trimethoxyphenyl)benzothieno[3,2-b]pyridine 5,5-dioxide
  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：

  苯并[b]噻吩-3(2H)-酮-1,1-二氧化物 在 哌啶 、 溶剂黄146 作用下， 反应 1.5h， 生成 3-ethoxycarbonyl-2-methyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxide
  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.