2,6-di(3-pyridylmethylidene)cyclohexanone | 132727-07-2

• 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-di(3-pyridylmethylidene)cyclohexanone
• 英文别名: 2,6-di(3-pyridylmethylene)cyclohexanone；2,5-bis-pyridine-3-ylmethylenecyclohexanone；2,6-bis-pyridin-3-ylmethylene-cyclohexanone；2,6-Bis--cyclohexanon；2,6-Bis(pyridin-3-ylmethylidene)cyclohexan-1-one
• CAS: 132727-07-2
• 化学式: C₁₈H₁₆N₂O
• mdl: MFCD00564623
• 分子量: 276.338
• InChiKey: LYDLODGAUHPYGN-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  500.9±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：

  silver trifluoromethanesulfonate 、 2,6-di(3-pyridylmethylidene)cyclohexanone 以 二氯甲烷 、 乙腈 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Coordination polymers of silver(I) with ditopic cross-conjugated dienone

  摘要：

  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.

  DOI：

  10.1134/s0036023617120038
• 作为产物：
  描述：

  3-吡啶甲醛 、 环己酮 在 盐酸 、 溶剂黄146 作用下， 反应 12.0h， 生成 2,6-di(3-pyridylmethylidene)cyclohexanone
  参考文献：
  名称：

  [EN] SMALL MOLECULE STIMULATORS OF STEROID RECEPTOR COACTIVATOR PROTEINS AND THEIR USE IN THE TREATMENT OF CANCER
  [FR] STIMULATEURS À PETITES MOLÉCULES DES PROTÉINES CO-ACTIVATRICES DES RÉCEPTEURS DE STÉROÏDES ET MÉTHODES POUR LES UTILISER

  摘要：

  提供了激活类固醇受体共激活蛋白（SRC）家族蛋白的小分子刺激剂，以及它们在治疗或预防癌症中的使用方法。还提供了在细胞中刺激SRC家族蛋白的方法。

  公开号：

  WO2016109470A1

文献信息

• 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。
• Design, Synthesis, and Photoluminescence Properties of One-, Two-, and Three-Dimensional Coordination Polymers: Anion-Assisted Argentophillic Interactions as Building Blocks
  作者：Kaustuv Banerjee、Sandipan Roy、Kumar Biradha

  DOI：10.1021/cg500898c

  日期：2014.10.1

  Five new Ag(I) complexes of the formulae [Ag-2(L-1)(2)(NDS)](3)H2O}(n) (1), [Ag-2(L-2)(2)(NDS)]center dot 2H2O}(n) (2), [Ag-3(L-2)(2)(IQS)(2)]center dot(NO3)center dot 4H(2)O center dot 2MeOH}(n) (3), [Ag-2(L-3)(2)(NDS)]center dot 4H(2)O}(n) (4), and [Ag-2(L-3)(2)(IQS)]center dot(NO3)center dot H2O}(n) (5) (L-1 = 2,5-bis-pyridine-3-ylmethylene-cyclopentanone, L-2 = 2,5-bis-pyridine-3-ylmethylene-cyclohexanone, L-3 = 2,5-bis-pyridine-4-ylmethylene-cyclopentanone, NDS = naphthalene disulfonate, and IQS = isoquinoline-5-sulfonate) have been synthesized and characterized by elemental analysis, IR, powder X-ray diffraction, and single-crystal X-ray diffraction. Complexes 13 were found to have sulfonate supported Ag center dot center dot center dot Ag interaction, and the sulfonate ions act as linkers to form higher dimensional networks (ladder, two- and three-dimensional networks). The complexes 4 and 5, which contain 4-pyridyl substitution, do not form such Ag center dot center dot center dot Ag interactions, indicating a clear tendency of 3-pyridyl derivatives to promote such interactions over 4-pyridyl derivatives. This observation was also evidenced by the analysis of Ag(I) complexes in Cambridge Structural Database. Further, complexes 15 were found to exhibit solid-state photoluminescence in the green region at room temperature.
• A temperature study on a stereoselective organocatalyzed aldol reaction in water
  作者：Enrico Emer、Paola Galletti、Daria Giacomini

  DOI：10.1016/j.tet.2008.09.059

  日期：2008.12

  We report the first temperature Study on the stereoselectivity of the 'in-water' aldol reaction between nicotinaldehyde (3-pyridinecarbaldehyde) and cyclohexanone catalyzed by morpholine and trans-4-tert-butyldimethylsilyloxy-L-proline. Eyring plots of diastereomeric ratio anti/syn gave a constant diastereoselectivity with respect to reaction temperature using morpholine as catalyst. With O(TBS)-L-proline we observed a non-linear behaviour of the Eyring plot with the presence of an inversion temperature (T-inv), which disclosed dynamic solvation effects in water. (C) 2008 Elsevier Ltd. All rights reserved.
• [EN] SMALL MOLECULE STIMULATORS OF STEROID RECEPTOR COACTIVATOR PROTEINS AND THEIR USE IN THE TREATMENT OF CANCER<br/>[FR] STIMULATEURS À PETITES MOLÉCULES DES PROTÉINES CO-ACTIVATRICES DES RÉCEPTEURS DE STÉROÏDES ET MÉTHODES POUR LES UTILISER
  申请人：BAYLOR COLLEGE MEDICINE

  公开号：WO2016109470A1

  公开（公告）日：2016-07-07

  Small molecule stimulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing cancer. Also provided are methods for stimulating SRC family proteins in a cell.

  提供了激活类固醇受体共激活蛋白（SRC）家族蛋白的小分子刺激剂，以及它们在治疗或预防癌症中的使用方法。还提供了在细胞中刺激SRC家族蛋白的方法。
• 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.