(2E,5E)-2,5-bis(4-bromobenzylidene)cyclopentanone | 58003-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,5E)-2,5-bis(4-bromobenzylidene)cyclopentanone
• 英文别名: 2,5-bis(4-bromobenzylidene)cyclopentanone；2,5-[(E,E)-bis-(4-bromo-benzylidene)]-cyclopentanone；2,5-[(E,E)-Bis-(4-brom-benzyliden)]-cyclopentanon；(2E,5E)-2,5-bis[(4-bromophenyl)methylidene]cyclopentan-1-one
• CAS: 58003-30-8；140401-80-5
• 化学式: C₁₉H₁₄Br₂O
• 分子量: 418.128
• InChiKey: GCQBWBIALSMYGO-JOBJLJCHSA-N

物化性质

• 熔点：
  251-253 °C(Solv: ethanol (64-17-5))
• 沸点：
  552.3±50.0 °C(Predicted)
• 密度：
  1.74 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-甲苯磺酰乙腈 、 (2E,5E)-2,5-bis(4-bromobenzylidene)cyclopentanone 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到1,2-bis(4-(4-bromophenyl)-1H-pyrrol-3-yl)ethane
  参考文献：
  名称：

  Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

  摘要：

  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。

  DOI：

  10.1039/c3ob42570c
• 作为产物：
  描述：

  对溴苯甲醛 、 环戊酮 在 aluminum oxide 作用下， 反应 0.06h， 以99%的产率得到(2E,5E)-2,5-bis(4-bromobenzylidene)cyclopentanone
  参考文献：
  名称：

  微波辅助芳香醛与环酮的无溶剂交叉醛醇缩合反应

  摘要：

  描述了微波辐射下醛和环状酮的快速氧化铝促进的交叉羟醛缩合反应。该方法简单，有效且对环境无害，并且产率很高，并且没有任何自凝结。

  DOI：

  10.1007/s00706-004-0256-9

文献信息

• Expanding the Scope of Enantioselective FerroPHANE-Promoted [3+2] Annulations with α,β-Unsaturated Ketones
  作者：Nathalie Pinto、Mathilde Neel、Armen Panossian、Pascal Retailleau、Gilles Frison、Arnaud Voituriez、Angela Marinetti

  DOI：10.1002/chem.200901893

  日期：2010.1.18

  The planar chiral 2‐phospha[3]ferrocenophane I has been shown to be the first efficient nucleophilic organocatalyst for the enantioselective synthesis of cyclopentenylphosphonates, through [3+2] cyclizations between diethyl allenylphosphonate and α,β‐unsaturated ketones. The same catalyst has also been applied to the highly enantioselective [3+2] cyclizations of allenic esters with dibenzylideneacetone

  平面型手性2-磷[3]二茂铁卟啉I已被证明是环戊烯基膦酸酯对映选择性合成的第一个有效亲核有机催化剂，它通过二乙基烯丙基膦酸酯和α，β-不饱和酮之间的[3 + 2]环化反应来实现。同样的催化剂也已用于烯丙基酯与二亚苄基丙酮和类似的双烯酮的高度对映选择性[3 + 2]环化反应，从而生成具有单环或螺环结构的官能化环戊烯（ee 84–95％）。已经表明，所得环戊烯中的残留烯酮功能可参与随后的环化步骤，以提供空前的C 2。对称双环戊烯酮。为了深入了解FerroPHANE I作为手性催化剂在[3 + 2]环化反应中的行为，已通过DFT方法计算了主要的膦-丙二烯加合物在能量上最受青睐的异构体。强调了可能控制手性诱导过程的因素。
• A highly stereoselective, catalytic four-component synthesis of dispiroindolo-pyrrolidines/-imidazolidines via azomethine ylides
  作者：Sengodagounder Muthusamy、Singaravelan Ganesh Kumar

  DOI：10.1016/j.tet.2016.03.046

  日期：2016.5

  and stereochemistry of dispiroheterocyclic ring systems were confirmed based on the representative single-crystal X-ray analysis. These reactions involve the generation of intermolecular azomethine ylide intermediates and the subsequent 1,3-dipolar cycloaddition process with olefins or imines.

  在噻吩甲酸铜（I）作为催化剂存在下，进行了涉及重氮酰胺，胺，醛，外亚甲基/亚胺的四组分反应，从而以区域，化学和非对映选择性的方式，以高收率提供了二螺吲哚并吡咯烷/咪唑烷衍生物。基于代表性的单晶X射线分析证实了双螺杂环环系统的结构和立体化学。这些反应涉及分子间偶氮甲叶立德中间体的产生以及随后的与烯烃或亚胺的1，3-偶极环加成过程。
• SmI₃Catalyzed Condensation of Aliphatic Cycloketones and Aldehydes in Ionic Liquid
  作者：Xingliang Zheng、Yongmin Zhang

  DOI：10.1081/scc-120015572

  日期：2003.3

  SmI3 catalyzed condensation of aliphatic cycloketones and aldehydes was studied in ionic liquid. 2,5-Dibenzyldiene cyclopentanones and 2,6-dibenzyldienecyclohexanones were prepared in high yields under convenient conditions.
• 10.101.6/j.arabjc.2011.06.001
  作者：Amoozadeh, Ali、Tabrizian, Elham、Rahmani, Salman

  DOI：10.101.6/j.arabjc.2011.06.001

  日期：——
• 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.