3,5-bis[(E)-2,3-dichlorobenzylidene]-1-methyltetrahydropyridin-4(1H)-one | 1392316-57-2

• 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: 3,5-bis[(E)-2,3-dichlorobenzylidene]-1-methyltetrahydropyridin-4(1H)-one
• 英文别名: (3E,5E)-3,5-bis[(2,3-dichlorophenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 1392316-57-2
• 化学式: C₂₀H₁₅Cl₄NO
• 分子量: 427.157
• InChiKey: FRVVXWGPJRTPNB-VOMDNODZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 2,3-二氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3,5-bis[(E)-2,3-dichlorobenzylidene]-1-methyltetrahydropyridin-4(1H)-one
  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

• Catalytic Activity of (Fe<SUB>2</SUB>O<SUB>3</SUB>)-MCM-41-nPrNH<SUB>2</SUB> Magnetically Recoverable Nanocatalyst for the Synthesis of Phenylpyrido[4,3-d]Pyrimidins
  作者：Shahnaz Rostamizadeh、Nasrin Shadjou、Elyass Isapoor、Mohammad Hasanzadeh

  DOI：10.1166/jnn.2013.7582

  日期：2013.7.1

  A new series of phenylpyrido[4,3-d]pyrimidin-2-amin derivatives have been synthesised from the reaction of (E)-3,5-bis(benzylidene)-4-piperidones and guanidine carbonate in the presence of (Fe2O3)-MCM-41-nPrNH2 as a magnetically recoverable nanocatalyst under solvent free conditions. This catalyst was highly recyclable (up to 5 times) and was easily recovered from the reaction mixture using an external magnet without loss of activity. The prepared magnetic catalyst is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), and nitrogen physisorption measurements. Also all the structures of title compounds 3a–h were elucidated by comprehensive 1H NMR,13C NMR, IR and Mass spectra.

  在无溶剂条件下，以 (Fe2O3)-MCM-41-nPrNH2 为磁性可回收纳米催化剂，通过 (E)-3,5-双(亚苄基)-4-哌啶酮和碳酸胍的反应合成了一系列新的苯基吡啶并[4,3-d]嘧啶-2-氨基衍生物。这种催化剂具有很强的可回收性（最多可回收 5 次），使用外部磁铁就能轻松地从反应混合物中回收，且不会丧失活性。所制备的磁性催化剂通过傅立叶变换红外（FT-IR）、X 射线粉末衍射（XRD）和氮气物理吸附测量进行了表征。此外，标题化合物 3a-h 的结构也通过 1H、13C NMR、IR 和质谱得到了全面的阐明。
• Intermolecular C—H...O and C—H...<i>X</i>interactions in substituted spiroacenaphthylene structures
  作者：J. Suresh、R. Vishnupriya、S. Sivakumar、R. Ranjith Kumar、S. Athimoolam

  DOI：10.1107/s0108270112024584

  日期：2012.7.15

  In the three spiroacenaphthylene structures 5′′-[(E)-2,3-dichlorobenzylidene]-7′-(2,3-dichlorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C₃₅H₂₆Cl₄N₂O₂S, (I), 5′′-[(E)-4-fluorobenzylidene]-7′-(4-fluorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C₃₅H₂₈F₂N₂O₂S, (II), and 5′′-[(E)-4-bromobenzylidene]-7′-(4-bromophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C₃₅H₂₈Br₂N₂O₂S, (III), the substituted aryl groups are 2,3-dichloro-, 4-fluoro- and 4-bromophenyl, respectively. The six-membered piperidine ring in all three structures adopts a half-chair conformation, the thiazolidine ring adopts a slightly twisted envelope and the pyrrolidine ring an envelope conformation; in each case, the C atom linking the rings is the flap atom. In all three structures, weak intramolecular C—H...O interactions are present. The crystal packing is stabilized through a number of intermolecular C—H...O and C—H...Xinteractions, whereX= Cl in (I) and F or S in (II), and C—H...O interactions are observed predominantly in (III). In all three structures, molecules are linked through centrosymmetric ring motifs, further tailored through a relay of C—H...X[Cl in (I), Br in (II) and O in (III)] interactions.

  在三种螺苊烯结构中，5′′-[(E)-2,3-二氯亚苄基]-7′-(2,3-二氯苯基)-1′′-甲基二螺[苊烯-1,5′-吡咯并[1,2-c][1,3]噻唑-6′、3′′-哌啶]-2,4′′-二酮，C35H26Cl4N2O2S，(I)，5′′-[(E)-4-氟亚苄基]-7′-(4-氟苯基)-1′′-甲基二螺[苊烯-1,5′-吡咯并[1,2-c][1、(II)，以及 5′′-[(E)-4-溴亚苄基]-7′-(4-溴苯基)-1′′-甲基二螺[苊烯-1,5′-吡咯并[1,2-c][1,3]噻唑]-2,4′′-二酮，C35H28F2N2O2S，(II)2-c][1,3]噻唑-6′,3′′-哌啶]-2,4′′-二酮，C35H28Br2N2O2S，(Ⅲ)，取代的芳基分别为 2,3-二氯、4-氟和 4-溴苯基。这三种结构中的六元哌啶环都采用了半对椅构象，噻唑烷环采用了略微扭曲的包络构象，而吡咯烷环则采用了包络构象；在每种情况下，连接环的 C 原子都是襟翼原子。在所有这三种结构中，都存在微弱的分子内 C-H...O 相互作用。晶体结构通过一些分子间的 C-H...O 和 C-H...X 相互作用得到稳定，其中 (I) 中的 X= Cl，(II) 中的 X= F 或 S，(III) 中主要观察到 C-H...O 相互作用。在所有这三种结构中，分子都是通过中心对称环图案连接起来的，并通过 C-H...X[(I) 中为 Cl，(II) 中为 Br，(III) 中为 O]相互作用的中继作用进一步调整。
• 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.
• An atom economic synthesis and AChE inhibitory activity of novel dispiro 7-aryltetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole and 4-aryloctahydroindolizine N-methylpiperidin-4-one hybrid heterocycles
  作者：Sathiyamoorthi Sivakumar、Raju Ranjith Kumar、Mohamed Ashraf Ali、Tan Soo Choon

  DOI：10.1016/j.ejmech.2013.04.050

  日期：2013.7

  The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and alpha-amino acids viz. 1,3-thiazolone-4-carboxylic acid and piperidine-2-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro[5.2 '']acenaphthene-1 ''-onespiro[6.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-7-aryltetrahydro-1H-pyrrolo[12-c][1,3]thiazoles and spiro[2.2 '']acenaphthene-1 ''-onespiro[3.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-4-aryloctahydroindolizines respectively in quantitative yields. These compounds were evaluated for their AChE inhibitory activity and compound 3c was found to be the most potent with IC50 1.86 mu mol/L. (C) 2013 Elsevier Masson SAS. All rights reserved.