(E,E)-2,5-bis(pyridin-4-ylmethylidene)cyclopentanone | 835604-56-3

• 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: (E,E)-2,5-bis(pyridin-4-ylmethylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(pyridine-4-methylene)cyclopentanone；(E,E)-2,5-bis((4-pyridyl)methylidene)cyclopentanone；2,5-bis[(E)-(4-pyridyl)methylidene]cyclopentanone；dpmcp；(2E,6E)-2,6-bis(pyridin-4-methylene)cyclopentanone；(2E,5E)-2,5-bis(pyridin-4-ylmethylene)cyclopentanone；(2E,5E)-2,5-bis(pyridin-4-ylmethylidene)cyclopentan-1-one
• CAS: 835604-56-3
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: VJTIKIQJUZWNSW-JOBJLJCHSA-N

物化性质

• 熔点：
  118 °C(Solv: ethanol (64-17-5))
• 沸点：
  512.0±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E,E)-2,5-bis(pyridin-4-ylmethylidene)cyclopentanone 生成 (2E,5E)-2,5-bis[(1-methylpyridin-1-ium-4-yl)methylidene]cyclopentan-1-one;diiodide
  参考文献：
  名称：

  KATRITZKY, ALAN R.;FAN, WEI-QIANG;JIAO, XUE-SHUN;LI, QIAO-LING, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1321-1325

  摘要：

  DOI：
• 作为产物：
  描述：

  4-吡啶甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 10.0h， 以50%的产率得到(E,E)-2,5-bis(pyridin-4-ylmethylidene)cyclopentanone
  参考文献：
  名称：

  衍生自环酮和芳香醛的交叉共轭二烯酮的合成、光谱和结构研究

  摘要：

  交叉共轭二烯酮是通过环状酮与两当量的芳香醛在碱性条件下反应合成的。NMR 光谱研究和 X 射线衍射分析表明，所有反应产物均以 E、E 异构体的形式形成。首次观察到溶液中散射光下交叉共轭二烯酮的自发光化学反顺异构化。异构化程度主要取决于二烯酮分子中心片段的性质。合成了以前未知的 2,5-双 [(E)-(3-吡啶基) 亚甲基] 环戊酮的光化学 [2+2]-环加成产物，并通过光谱方法和 X 射线衍射进行了表征。在所使用的条件下，仅获得环丁烷加合物的一种异构体。

  DOI：

  10.1007/s11172-006-0397-6

文献信息

• Synthesis and hydrophosphorylation of π-complexes of dibenzylideneacetone and cyclic conjugated dienones with homocarbonyl and carbonylcyclopentadienyl molybdenum compounds
  作者：A. I. Kuramshin、S. Z. Vatsadze、V. I. Galkin、R. A. Cherkasov

  DOI：10.1134/s1070363216030221

  日期：2016.3

  Reactions of dibenzylideneacetone and cyclic cross-conjugated dienones with hexacarbonylmolybdenum(0) and bis[tricarbonyl(cyclopentadienyl)molybdenum(0)] afforded the corresponding complexes with η2-(C=C),η2-(C=O) coordination of the diketone to metal center, regardless of the ligand structure and initial molybdenum compound. The reactivity of the multidentate ligands may change as a result of coordination

  二亚苄和环状交叉偶联二烯酮的反应，与hexacarbonylmolybdenum（0）和二[三羰基（环戊二烯基）钼（0）]与得到相应的络合物η 2 - （C = C），η 2 - （C = O）的协调从二酮到金属中心，无论配体结构和初始钼化合物如何。多齿配体的反应性可能由于配位而改变。
• 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.
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Ruthenium arene complexes with mono-carbonyl analogues of curcumin as pendant or bridging ligands: Synthesis, anti-cancer activity and interaction with quadruplex DNA
  作者：Jiaming Bi、Tianle Pay、Zhen Xuan Wong、Yan Yi Khong、Ming Xuan Kueh、Kai Jie Ng、Peter P.F. Lee、Yong Leng Kelvin Tan

  DOI：10.1016/j.poly.2019.07.034

  日期：2019.10

  Four ruthenium(II) arene complexes containing mono-carbonyl analogues of curcumin (MAC) functioning as pendant or bridging ligands as well as chlorido ancillary ligands have been synthesized and structurally characterized by IR and H-1 NMR spectroscopies, ESI mass spectrometry and elemental analysis. Anti-proliferative activity of the complexes determined on MOLT-4 human leukemia cells revealed good to moderate activity. Two of the compounds, 3b and 4b, both of which incorporated cyclohexanone as part of the MAC structural motif, displayed potency comparable to cisplatin. In intercalative binding studies, while the organic MACs did not display any interaction with quadruplex DNA, the ruthenium complexes were found to be able to stabilize quadruplex DNA, with 3b and 4b displaying the greatest selectivity for HTelo over c-myc. Compound 4b, in which the MAC ligand is bridged by two organoruthenium centres, bound to HTelo more tightly than 3b, in which the MAC functions as a pendant ligand towards a single ruthenium arene core. These results suggest that minor changes to the structural motif of the MAC ligand, as well as the presence of the ruthenium arene moiety play an important role in achieving selective quadruplex DNA stabilization. (C) 2019 Elsevier Ltd. All rights reserved.
• Synthesis and spectroscopic and structural studies of cross-conjugated dienones derived from cyclic ketones and aromatic aldehydes
  作者：S. Z. Vatsadze、M. A. Manaenkova、N. V. Sviridenkova、N. V. Zyk、D. P. Krut’ko、A. V. Churakov、M. Yu. Antipin、J. A. K. Howard、H. Lang

  DOI：10.1007/s11172-006-0397-6

  日期：2006.7

  Cross-conjugated dienones were synthesized by the reactions of cyclic ketones with two equivalents of aromatic aldehydes under basic conditions. An NMR spectroscopic study and X-ray diffraction analysis demonstrated that all reaction products are formed as E,E isomers. Spontaneous photochemical trans-cis isomerization of cross-conjugated dienones under the scattered light in solution was observed for

  交叉共轭二烯酮是通过环状酮与两当量的芳香醛在碱性条件下反应合成的。NMR 光谱研究和 X 射线衍射分析表明，所有反应产物均以 E、E 异构体的形式形成。首次观察到溶液中散射光下交叉共轭二烯酮的自发光化学反顺异构化。异构化程度主要取决于二烯酮分子中心片段的性质。合成了以前未知的 2,5-双 [(E)-(3-吡啶基) 亚甲基] 环戊酮的光化学 [2+2]-环加成产物，并通过光谱方法和 X 射线衍射进行了表征。在所使用的条件下，仅获得环丁烷加合物的一种异构体。