N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone | 142808-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone
• 英文别名: N-methyl-3,5-di(4-pyridylmethylene)piperidine-4-one；1-methyl-3,5-bis(4'-pyridylmethylene)-4-piperidone；6383479；4-Piperidinone, 1-methyl-3,5-bis(4-pyridinylmethylene)-；1-methyl-3,5-bis(pyridin-4-ylmethylidene)piperidin-4-one
• CAS: 142808-60-4
• 化学式: C₁₈H₁₇N₃O
• mdl: MFCD03450139
• 分子量: 291.352
• InChiKey: PFSHGYYOLVTIGM-UHFFFAOYSA-N

物化性质

• 沸点：
  526.3±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 1.67h， 生成
  参考文献：
  名称：

  碱性离子液体[BMIM] OH催化微波促进简便有效地合成哌啶子[3'，4'：5,6]吡喃并[2,3-d]嘧啶酮

  摘要：

  碱性离子液体[BMIM] OH可以非常有效地催化吡喃并[3,2-c]哌啶类似物和羰基化合物合成哌啶并[3'，4'：5,6]吡喃并[2,3-d]嘧啶酮衍生物化合物。[BMIM] OH既起着催化剂的作用，又起着反应介质的作用，可以进行五次反应，而催化效率没有任何明显的降低。微波和离子液体的协同作用在非常短的反应时间内即可提供高产率的产品，并且易于后处理。

  DOI：

  10.1016/j.molcata.2013.10.026
• 作为产物：
  描述：

  4-吡啶甲醛 、 N-甲基-4-哌啶酮 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 0.17h， 生成 N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone
  参考文献：
  名称：

  碱性离子液体[BMIM] OH催化微波促进简便有效地合成哌啶子[3'，4'：5,6]吡喃并[2,3-d]嘧啶酮

  摘要：

  碱性离子液体[BMIM] OH可以非常有效地催化吡喃并[3,2-c]哌啶类似物和羰基化合物合成哌啶并[3'，4'：5,6]吡喃并[2,3-d]嘧啶酮衍生物化合物。[BMIM] OH既起着催化剂的作用，又起着反应介质的作用，可以进行五次反应，而催化效率没有任何明显的降低。微波和离子液体的协同作用在非常短的反应时间内即可提供高产率的产品，并且易于后处理。

  DOI：

  10.1016/j.molcata.2013.10.026

文献信息

• Cocrystals and Salts of 3,5-Bis(pyridinylmethylene)piperidin-4-one with Aromatic Poly-Carboxylates and Resorcinols: Influence of Stacking Interactions on Solid-State Luminescence Properties
  作者：Debarati Das、Kumar Biradha

  DOI：10.1071/ch19062

  日期：——

  resorcinol derivatives displayed O–H⋯N hydrogen bonding to form tetrameric aggregates of bis-pyridyl ketone molecules and respective co-formers, while 3,5-dihydroxy benzoic acid (DHBA) molecules formed 1D chains by clipping two molecules of ketones with three DHBA molecules. Such clipping by the resorcinol derivatives promoted continuous π–π stacking interactions. Consequently, these materials emitted

  显示了两个双吡啶基取代的α，β-不饱和酮与羧酸和间苯二酚衍生物形成络合物。仅在一个复杂的出含有这里所研究复合物的五个酸-双-吡啶基的观察中性酸-酸homosynthon，而-COO -发现⋯HOOC-合成子是主要的，因为在四个复合物中观察到。羧酸盐自组装形成离散的二聚，阴离子一维链，并且还表现出混合的离子氢键。另一方面，间苯二酚衍生物显示出O–H⋯N氢键，形成双吡啶酮分子和各自的共形成物的四聚体聚集体，而3,5-二羟基苯甲酸（DHBA）分子则通过截断两个分子而形成一维链。带有三个DHBA分子的酮 间苯二酚衍生物的这种截留促进了连续的π-π堆积相互作用。因此，与母体双吡啶基取代的α，β-不饱和酮相比，这些材料以更高的波长发射。
• Synthesis, structure, antitumor activity of novel pharmaceutical co-crystals based on bispyridyl-substituted α, β-unsaturated ketones with gallic acid
  作者：Lian-Dong Liu、Shu-Lian Liu、Zhi-Xian Liu、Gui-Ge Hou

  DOI：10.1016/j.molstruc.2016.02.025

  日期：2016.5

  Abstract Three novel pharmaceutical co-crystals, (A)·(gallic acid) ( 1 ), (B)·(gallic acid) ( 2 ), and (C)·(gallic acid) ( 3 ) were generated based on 2,6-bis((pyridin-4-yl)methylene)cyclohexanone (A), N -methyl-3,5-bis((pyridin-3-yl)methylene)-4-piperidone (B), N -methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone (C) with gallic acid, respectively. They are characterized by elemental analysis,

  摘要 基于2, 制备了三种新型药物共晶, (A)·(没食子酸) ( 1 ), (B)·(没食子酸) ( 2 ), (C)·(没食子酸) ( 3 ), 6-双((吡啶-4-基)亚甲基)环己酮 (A), N-甲基-3,5-双((吡啶-3-基)亚甲基)-4-哌啶酮 (B), N-甲基-3 ,5-双((吡啶-4-基)亚甲基)-4-哌啶酮(C)分别与没食子酸。它们的特征在于元素分析、FTIR 光谱、 1 H NMR 和单晶 X 射线衍射。结构分析表明，两种药物成分在 1、2 或 3 中的 2D 平面中相互连接成 H 键驱动的 3D 网络。此外，主要评估了它们对人肿瘤细胞系 A549、SGC-7901、MCF-7、OVCA-433、HePG2 的抗肿瘤活性以及通过 CCK-8 方法对 HUVEC 细胞系的细胞毒性。与没食子酸和游离A、B、C相比，它们的抗肿瘤活性明显提高，而细胞毒性明显降低，特别是对于共晶
• Dimmock; Arora; Semple, Pharmazie, 1992, vol. 47, # 4, p. 246 - 248
  作者：Dimmock、Arora、Semple、Lee、Allen、Kao

  DOI：——

  日期：——
• Coordination polymers of silver(I) with ditopic cross-conjugated dienone
  作者：A. A. M. Aly、S. Z. Vatsadze、B. Walfort、T. Rüffer、H. Lang

  DOI：10.1134/s0036023617120038

  日期：2017.12

  The reaction of the silver salts AgX (a: X = BF4 (-), b: X = ClO4 (-), c: X = OTf-) with alpha,alpha'-di(3/4-pyridylmethylene)cycloalkanones (L-1-L-3) and piperidones (L-4-L-7) results in the formation of coordination products of general composition [AgX(L (n) )(solvent)] and [AgX(L (n) )] (L (n) = L-1-L-7). All complexes were characterized by elemental analysis and IR-spectroscopy. The structures of [Ag(ClO4)(L-1)(MeCae N)](a) (1b center dot MeCae N) and [Ag(ClO4)(L-1)](a) (1b) in the solid state are reported. In both structures Ag(L-1)}(+) building units are linked to each other via Ag-N-pyridine primary bonds resulting in the formation of infinite chains. In both structures the ligands L-1 are fixed in transoid conformations, thus forming zig-zag polar chains. The structure of 1b center dot MeCae N consists of pairs of tightly and loosely stacked chains. The tightly packed chains are weakly coupled by perchlorate anions acting as mu-bridges in between Ag(I) centers as well as by pi-pi-stacking interactions of unsaturated fragments of the respective ligands. In contrast, polar 2D layers composed of Ag(L-1)} (m) (m+) chains, which interdigitate via multiple weak interactions by Ag-O contacts, are found in the solid structure of 1b. The dissolution of coordination products in coordinating solvents like MeCN or DMSO leads to the decomposition of complexes due to formation of silver-solvent coordination compounds. The coordination products 1-5 are stable in solid state against exposure to the ambient light, whereas solutions of the compounds, especially in DMSO-d (6), appeared to be photochemically labile. As revealed by NMR spectroscopic studies, the organic components undergo trans-cis isomerization.