(8E)-2-amino-8-(2,3-dichlorobenzylidene)-4-(2,3-dichlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile | 1399845-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8E)-2-amino-8-(2,3-dichlorobenzylidene)-4-(2,3-dichlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile
• 英文别名: (8E)-8-(2,3-dichlorobenzylidene)-2-amino-4-(2,3-dichlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile；(8E)-2-amino-4-(2,3-dichlorophenyl)-8-[(2,3-dichlorophenyl)methylidene]-6-methyl-5,7-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile
• CAS: 1399845-67-0
• 化学式: C₂₃H₁₇Cl₄N₃O
• 分子量: 493.219
• InChiKey: PMDLGJPVOJSRRD-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-bis[(E)-2,3-dichlorobenzylidene]-1-methyltetrahydropyridin-4(1H)-one 、 丙二腈 在 mesoporous MCM-41-SO₃H 作用下， 反应 0.17h， 以98%的产率得到(8E)-2-amino-8-(2,3-dichlorobenzylidene)-4-(2,3-dichlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile
  参考文献：
  名称：

  MCM-41-SO3H作为高级纳米催化剂在无溶剂合成吡喃并[3,2-c]吡啶衍生物中的应用

  摘要：

  MCM-41-SO 3 H，一种有序的介孔二氧化硅材料，其中具有共价锚定磺酸基团的MCM-41被用作酸性催化剂，可在以下条件下快速并“绿色”合成吡喃并[3,2-c]吡啶衍生物无溶剂条件。与文献报道的常规方法相比，该新颖的合成方法的优点是催化剂的可重复使用性，高产率，短反应时间，简单和易于后处理。

  DOI：

  10.1002/jccs.201100667

文献信息

• Efficient synthesis of pyrano[3,2-c]pyridines via a green and catalyst-free method at ambient temperature, and related DFT calculations
  作者：Shahnaz Rostamizadeh、M. Z. Kassaee、Nasrin Shadjou、Hassan Zandi

  DOI：10.1007/s00706-012-0851-0

  日期：2013.5

  Twelve medicinally important pyrano[3,2-c]pyridine derivatives were precipitated, with high yields, from ethanol solutions of malononitrile and (E)-3,5-bis(benzylidene)-4-piperidones at ambient temperature, requiring almost no work-up. Natural bond order calculations at the B3LYP/6-31+G* level indicate that electron-withdrawing groups on the phenyl rings deplete electron density on beta-atoms (with respect to the carbonyl groups) of the piperidones, leading to higher yields of the corresponding products with shorter reaction times. This green methodology appears in a clear contrast to all previous reports, where either a catalyst and/or microwave was employed. So, simplicity and short reaction time, non-toxicity of the solvent, as well as economic feasibility are major advantages of this chemically waste-free process.