2,2'-bis(4-pyridylmethylidene)cyclopentanone | 108977-83-9

• 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: 2,2'-bis(4-pyridylmethylidene)cyclopentanone
• 英文别名: 2,5-di(4-pyridylmethylidene)cyclopentanone；2,5-bis-pyridine-4-ylmethylenecyclopentanone；2,5-bis-pyridin-4-ylmethylene-cyclopentanone；2,5-Bis--cyclopentanon；Cyclopentanone, 2,5-bis(4-pyridinylmethylene)-, (2E,5E)-；2,5-bis(pyridin-4-ylmethylidene)cyclopentan-1-one
• CAS: 108977-83-9
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: VJTIKIQJUZWNSW-UHFFFAOYSA-N

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：

  2,2'-bis(4-pyridylmethylidene)cyclopentanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以78%的产率得到2,2'-bis(4-pyridylmethylidene)cyclopentanol
  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：
• 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 5.0h， 生成 2,2'-bis(4-pyridylmethylidene)cyclopentanone
  参考文献：
  名称：

  Design, Synthesis, and Photoluminescence Properties of One-, Two-, and Three-Dimensional Coordination Polymers: Anion-Assisted Argentophillic Interactions as Building Blocks

  摘要：

  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.

  DOI：

  10.1021/cg500898c

文献信息

• 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.
• Katritzky, Alan R.; Fan, Wei-Qiang; Jiao, Xue-Shun, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1321 - 1325
  作者：Katritzky, Alan R.、Fan, Wei-Qiang、Jiao, Xue-Shun、Li, Qiao-Ling

  DOI：——

  日期：——
• 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.