2,6-bis(pyridin-4-ylmethylene)cyclohexan-1-one | 18977-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-bis(pyridin-4-ylmethylene)cyclohexan-1-one
• 英文别名: 2,6-bis((pyridin-4-yl)methylene)cyclohexanone；2,6-bis(4-pyridylmethylidene)cyclohexanone；2,6-di(4-pyridylmethylidene)cyclohexanone；2,6-di(4-pyridylmethylene)cyclohexanone；6018993；2,6-bis-pyridin-4-ylmethylene-cyclohexanone；Cyclohexanone, 2,6-bis(4-pyridinylmethylene)-, (2E,6E)-；2,6-bis(pyridin-4-ylmethylidene)cyclohexan-1-one
• CAS: 18977-41-8
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: CYVVJSKZRBZHAV-UHFFFAOYSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  514.5±50.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 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：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(pyridin-4-ylmethylene)cyclohexan-1-one 在 sodium acetate 、 乙酸酐 、 sulfur 、 溶剂黄146 、 二乙胺 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 56.0h， 生成
  参考文献：
  名称：

  设计，合成和鉴定新型取代的异硫代色素类似物作为潜在的抗病毒和细胞毒性药物

  摘要：

  摘要在这项研究中，我们介绍了基于原料3-氨基-异硫代色烯-4-甲腈3的新型异硫代色酮，噻唑酮，噻嗪酮，芳基，三唑和嘧啶酮化合物的合成。使用光谱法和元素分析确认化学结构。筛选这些化合物的体外抗病毒和抗肿瘤活性。化合物10a-c和22a-b显示出对单纯疱疹病毒1（HSV-1）和人类免疫缺陷病毒1（HIV-1）的活性。化合物15和21a-b显示出对各种类型的癌细胞系的活性。 化合物22a-b和10a-c对单纯疱疹病毒1（HSV-1）和病毒1（HIV-1）具有活性。同样，产物21a-b和15被证明在很大程度上具有抗肿瘤活性。

  DOI：

  10.1007/s00044-018-2236-3
• 作为产物：
  描述：

  4-吡啶甲醛 、 环己酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 10.0h， 以82%的产率得到2,6-bis(pyridin-4-ylmethylene)cyclohexan-1-one
  参考文献：
  名称：

  Katritzky, Alan R.; Fan, Wei-Qiang; Jiao, Xue-Shun, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1321 - 1325

  摘要：

  DOI：

文献信息

• A Photoswitchable and Photoluminescent Organic Semiconductor Based On Cation-π and Carboxylate-Pyridinium Interactions: A Supramolecular Approach
  作者：Sandipan Roy、Suvra Prakash Mondal、Samit K. Ray、Kumar Biradha

  DOI：10.1002/anie.201205822

  日期：2012.11.26

  More than the sum of the parts: The property of a supramolecular material can differ significantly from those of the constituent materials. Two organic components, which are nonconductive, nonphotochromic, and nonluminescent, were shown to self‐assemble by cation–π, π–π, and carboxylate–pyridinium interactions. An organic semiconductor is thus produced with significant charge mobility and photochromic

  超过各部分的总和：超分子材料的性质可能与构成材料的性质显着不同。非有机，非光致变色和不发光的两种有机成分通过阳离子-π，π-π和羧酸根-吡啶鎓相互作用自组装。因此产生具有显着的电荷迁移率以及光致变色和光致发光性质的有机半导体。
• 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
• Metal–organic frameworks constructed using acid–base mixed ligands, carboxylic acids and N-containing chalcone, and their catalytic performance for Knoevenagel condensation
  作者：Limin Cheng、Junyong Zhang、Caihong Zhan、Hao Xu、Chunhua Gong、Jingli Xie

  DOI：10.1039/d3nj05164a

  日期：——

  layered structures and serve as an efficient and economical porous heterogeneous catalyst for Knoevenagel condensation under mild conditions. The yields of Knoevenagel condensation can be reached between 96% and 99% in the presence of catalysts 1–3. Notably, the catalytic performance of 1 through reusability was explored, and it was observed that 1 could be reused up to six cycles with almost consistent

  采用混合配体策略，通过溶剂热反应构建了三种金属有机框架。这些化合物表现出类似的二维层状结构，可作为温和条件下克诺文格尔缩合的高效且经济的多孔非均相催化剂。在催化剂1-3存在下，Knoevenagel 缩合的收率可以达到 96% 至 99% 。值得注意的是，通过可重复使用性探索了1的催化性能，并观察到​​1可以重复使用最多六个循环，且催化效率几乎一致。
• Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones
  作者：Saulo F.P. Braga、Érika V.P. Alves、Rafaela S. Ferreira、Jordana R.B. Fradico、Paula S. Lage、Mariana C. Duarte、Tatiana G. Ribeiro、Policarpo A.S. Júnior、Alvaro J. Romanha、Maiko L. Tonini、Mário Steindel、Eduardo F. Coelho、Renata B. de Oliveira

  DOI：10.1016/j.ejmech.2013.11.011

  日期：2014.1

  A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 mu M. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 mu M). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (<= 1.2 mu M) with an adequate SI (>= 19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Organometallic π-tweezers incorporating pyrazine- and pyridine-based bridging units
  作者：M. Al-Anber、Th. Stein、S. Vatsadze、H. Lang

  DOI：10.1016/j.ica.2004.07.054

  日期：2005.1

  Pyrazine- and pyridine-based pi-conjugated sigma-donor molecules, such as 4,4'-bipyridine, 1,2-di(4-pyridyl)ethylene, 3,5-dipyridyl-1,2,4-triazole, N,N'-bis(4-pyridylmethylidene)benzene-1,4-diamine, 2,5-di(pyridylmethylidene)cyclopentanone, 2,6-di(4-pyridylmethylidene)cyclohexanone (LL, 2a-2g) can successfully be used to span heterobimetalfic pi-tweezer units of the type [[Ti](mu-sigma,piCequivalent toCSiMe(3))(2)}M](+) ([Ti] = (eta(5)-C5H4SiMe3)(2)Ti; M = Cu, Ag). The thus accessible di-cationic species [[Ti](mu-sigma,pi-Cequivalent toCSiMe(3))(2)} M-LL-M (Me(3)SiCequivalent toC-mu-sigma,pi)(2)[Ti]}](2+), (4), which are formed via the formation of [[Ti](mu-sigma,pi-Cequivalent toCSiMe(3))(2)}M-LL](+) (3) complexes, can be isolated in yields between 66% and 99%.However, when C5H4N-CH=CH-C6H4-CH=CH-NC5H4 (5a) and C5H4N-CH=N-C6H4-CH=CH-NC5H4 (5b), respectively, are reacted with [Ti](mu-sigma,pi-Cequivalent toCSiMe(3))(2)} AgBF4 (1c) in a 1: 1 molar ratio, then the silver(l) ion is released from the organometallic pi-tweezer 1c and coordination polymers [AgBF(4)(.)5a](n) (6a) and [AgBF(4)(.)5b](n) (6b) along with [Ti](Cequivalent toCSiMe(3))(2) (7) are formed in quantitative yield. (C) 2004 Elsevier B.V. All rights reserved.