α,α'-bis(m-pyridylmethylidene)cyclopentanone

• 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: α,α'-bis(m-pyridylmethylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(pyridin-3-ylmethylene)cyclopentanone；(2E,5E)-2,5-bis(pyridine-3-methylene)cyclopentanone；2,5-bis[(E)-(3-pyridyl)methylidene]cyclopentanone；2,5-bis[(E)-(3-pyridyl)methylene]cyclopentanone；2,5-bis(3-pyridylmethylene)-cyclopentanone；(2E,6E)-2,6-bis(pyridin-3-methylene)cyclopentanone；(2E,5E)-2,5-bis(pyridin-3-ylmethylidene)cyclopentan-1-one
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: VWOZSYQLWMRUOP-KAVGSWPWSA-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：

  α,α'-bis(m-pyridylmethylidene)cyclopentanone 以 四氯化碳 、 乙腈 为溶剂， 反应 730.5h， 生成 (2E,8E,5RS,6RS,11RS,12RS)-11,12-di(3-pyridyl)-2,8-bis[(3-pyridyl)methylidene]dispiro[4.0.4.2]dodecane-1,7-dione
  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
• 作为产物：
  描述：

  3-吡啶甲醛 、 环戊酮 在 ytterbium(III) triflate 作用下， 反应 7.0h， 以88%的产率得到α,α'-bis(m-pyridylmethylidene)cyclopentanone
  参考文献：
  名称：

  Yb(OTf)3催化无溶剂条件下方便合成α,α'-双(取代亚苄基)环烷酮

  摘要：

  在无溶剂条件下，在催化量的 Yb(OTf) 3 存在下，一系列芳香醛与酮发生交叉羟醛缩合反应，以优异的收率得到相应的 α,α'-双（取代亚苄基）环烷酮，而不会发生任何副反应。与使用许多经典路易斯酸的现有方法相比，该方法非常通用、简单且环保。此外，催化剂可以方便地回收和有效地重复使用而不损失活性。

  DOI：

  10.1055/s-2004-834900

文献信息

• A Convenient Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones Catalyzed by Yb(OTf)₃Under Solvent-Free Conditions
  作者：Limin Wang、Jia Sheng、He Tian、Jianwei Han、Zhaoyu Fan、Changtao Qian

  DOI：10.1055/s-2004-834900

  日期：——

  aromatic aldehydes undergoes crossed aldol condensation with ketones in the presence of a catalytic amount of Yb(OTf) 3 under solvent-free conditions to afford the corresponding α,α'-bis(substituted benzylidene)cycloalkanones in excellent yields without occurrence of any side reactions. This method is very general, simple and environmental friendly in contrast with the existing methods, which use many

  在无溶剂条件下，在催化量的 Yb(OTf) 3 存在下，一系列芳香醛与酮发生交叉羟醛缩合反应，以优异的收率得到相应的 α,α'-双（取代亚苄基）环烷酮，而不会发生任何副反应。与使用许多经典路易斯酸的现有方法相比，该方法非常通用、简单且环保。此外，催化剂可以方便地回收和有效地重复使用而不损失活性。
• Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)
  作者：Rong Wang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c3ob42570c

  日期：——

  A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C–C bond cleavage in the presence of water under mild conditions.

  本报告介绍了一种通过二烯酮衍生物与 TosMIC 反应获得 3,3-联吡咯衍生物的简单而高效的合成策略。该反应涉及 van Leusen 的吡咯合成，然后在温和的条件下，在有水存在的情况下进行不寻常的 CâC 键裂解。
• Anion Influence in Directing and Altering the Stereochemistry of the Double [2+2] Reaction of Bis-Pyridyl Dienes in their Silver Complexes: A Green Synthetic Route
  作者：Ramkinkar Santra、Mousumi Garai、Debiprasad Mondal、Kumar Biradha

  DOI：10.1002/chem.201201797

  日期：2013.1.7

  Getting selectively organized: Molecules of bis‐pyridyl dienes have been stereoselectively photodimerized to form their strained double [2+2] reaction products by using argentophilic forces (see scheme). A pronounced influence of anions and the efficiency of a mechanochemical synthesis have also been described.

  有选择地组织：双吡啶二烯分子已经立体选择性地光二聚化，通过使用亲银力使其形成应变的双[2 + 2]反应产物（请参阅方案）。还描述了阴离子的显着影响和机械化学合成的效率。
• 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.
• A binuclear silver(I) perchlorate macrocycle based on 2,5-bis[(E)-(3-pyridyl)methylene]cyclopentanone: Crystal structure and solution behavior
  作者：Aref A.M. Aly、Sergey Z. Vatsadze、Aleksey V. Chernikov、Bernhard Walfort、Tobias Rüffer、Heinrich Lang

  DOI：10.1016/j.poly.2007.04.045

  日期：2007.8

  The homobinuclear complex [Ag(MeC N)(OClO3)(mu-L)](2) (L = 2,5-bis[(E)-(3-pyridyl)methylene]cyclopentanone) (3) has been prepared by the diffusion-controlled reaction of [AgClO4] (1) dissolved in acetonitrile with equimolar amounts of L (2) in chloroform. The coordination complex 3 was characterized by single-crystal X-ray diffraction studies, showing that in the solid state a 26-membered disilver macrocycle is formed. The four coordination sites at the silver metal center are occupied by two nitrogen donor atoms of neighboring ligands, one nitrogen donor atom of an acetonitrile solvent molecule and an oxygen donor atom from a weakly-coordinated OClO3 counter-anion. During a 6 months period compound 3 in the solid state does not undergo any visible changes upon action of ambient light (NMR check), whilst dimethylsulfoxide (DMSO) solutions of 3 on exposure to sunlight undergo a rapid (ca. 1 day) photochemical transformation, namely trans/cis-isomerization and [2+2] cycloaddition reactions. This phenomenon is explained by the dissociation of 3 to the starting components 1 and 2 in DMSO and acetonitrile solutions, as has been demonstrated by H-1 NMR spectroscopy and ESI-TOF mass-spectrometry. (c) 2007 Elsevier Ltd. All rights reserved.