methyl 4,5-dihydro-2-methyl-4-(4-methylphenyl)-5-oxo-1H-indeno[1,2-b]pyridine-3-carboxylate | 443322-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: methyl 4,5-dihydro-2-methyl-4-(4-methylphenyl)-5-oxo-1H-indeno[1,2-b]pyridine-3-carboxylate
• 英文别名: methyl 2-methyl-4-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate；methyl 2-methyl-4-(4-methylphenyl)-5-oxo-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
• CAS: 443322-45-0
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: MQAJJYWKBLPPGG-UHFFFAOYSA-N

物化性质

• 沸点：
  537.8±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,5-dihydro-2-methyl-4-(4-methylphenyl)-5-oxo-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70%的产率得到methyl 4a-bromo-2-methyl-5-oxo-4-(4-methylphenyl)-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：

  methyl 4a-bromo-2-methyl-5-oxo-4-(4-methylphenyl)-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92%的产率得到methyl 4,5-dihydro-2-methyl-4-(4-methylphenyl)-5-oxo-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

• Tailor-made synthesis of fully alkylated/arylated nicotinates by FeCl₃-mediated condensation of enamino esters with enones
  作者：Sho Hirai、Yurie Horikawa、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1039/c7cc00051k

  日期：——

  A new method for synthesizing polyalkylated/arylated nicotinates is established using a condensation of enamino esters with enones in the presence of FeCl3. This method facilitates the introduction of alkyl or...

  在FeCl3存在下，使用烯胺酯与烯酮的缩合，建立了一种合成多烷基化/芳基烟酸酯的新方法。这种方法有助于引入烷基或...
• Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines
  作者：Subhasis Samai、Ganesh Chandra Nandi、Ram Kumar、M.S. Singh

  DOI：10.1016/j.tetlet.2009.10.022

  日期：2009.12

  A simple and efficient synthesis of 4-aryl-4,5-dihydro-1H-indeno[1,2-b]pyridine derivatives has been achieved via a four-component cyclocondensation of 1,3-indanedione, aromatic aldehydes, β-ketoesters and ammonium acetate in one-pot in the absence of catalyst and solvent at room temperature on grinding. The present approach offers several advantages such as shorter reaction times, higher yields, low

  通过1,3-茚满二酮，芳族醛，β-的四组分环缩合反应，可以实现4-芳基-4,5-二氢-1 H-茚并[1,2- b ]吡啶衍生物的简单有效合成在室温下，在不存在催化剂和溶剂的情况下，一锅法制得酮酯和乙酸铵。本方法具有几个优点，例如较短的反应时间，较高的产率，低成本，简单的后处理和容易的纯化。
• An eco-benign and highly efficient access to dihydro-1H-indeno[1,2-b]pyridines in 2,2,2-trifluoroethanol
  作者：Samad Khaksar、Milad Gholami

  DOI：10.1016/j.molliq.2014.03.030

  日期：2014.8

  4-Aryl-4,5-dihydro-1H-indeno[1,2-b]pyridine derivatives are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol in 2,2,2-trifluoroethanol (TFE). The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse. (C) 2014 Elsevier B.V. All rights reserved.