(2E,2'E)-1,1'-(1,4-亚苯基)二(3-苯基-2-丙烯-1-酮) | 34838-64-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: (2E,2'E)-1,1'-(1,4-亚苯基)二(3-苯基-2-丙烯-1-酮)
• 英文名称: (2E,2′E)-1,1′-(1,4-phenylene)bis(3-phenylprop-2-en-1-one)
• 英文别名: (E,E)-3-Phenyl-1-[4-(3-phenylpropenoyl)phenyl]-prop-2-en-1-on；(2E,2'E)-1,1'-(1,4-phenylene)bis(3-phenylprop-2-en-1-one)；1,1’-(1,4-phenylene)bis(3-phenylprop-2-en-1-one)；1,1'-(1,4-phenylene)bis(3-phenyl-2-propen-1-one)；1,4-dicinnamoylbenzene；1,4-dicynnamoylbenzene；(E)-3-phenyl-1-[4-[(E)-3-phenylprop-2-enoyl]phenyl]prop-2-en-1-one
• CAS: 34838-64-7
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: YDJKHVQLADEYIK-JYFOCSDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-1,1'-(1,4-亚苯基)二(3-苯基-2-丙烯-1-酮) 以 正庚烷 为溶剂， 反应 9.0h， 以57%的产率得到21,22,23,24-tetraphenyl-1,4,11,14-teraoxo-2(3),12(13)-diethano<4,4>paracyclophane
  参考文献：
  名称：

  通过拓扑化学方法对1,4-二肉桂基苯晶体进行光二聚化

  摘要：

  1，4-二肉桂基苯晶体通过双[2 + 2]环加成反应容易地光聚合成相应的三环二聚体，该三环二聚体由两个环丁烷环和一个由两个亚苯基键桥接的大环组成。

  DOI：

  10.1016/s0040-4039(00)99938-6
• 作为产物：
  描述：

  对二乙酰氧基苯 、 苯甲醛 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (2E,2'E)-1,1'-(1,4-亚苯基)二(3-苯基-2-丙烯-1-酮)
  参考文献：
  名称：

  通过拓扑化学方法对1,4-二肉桂基苯晶体进行光二聚化

  摘要：

  1，4-二肉桂基苯晶体通过双[2 + 2]环加成反应容易地光聚合成相应的三环二聚体，该三环二聚体由两个环丁烷环和一个由两个亚苯基键桥接的大环组成。

  DOI：

  10.1016/s0040-4039(00)99938-6

文献信息

• Practical metal-free synthesis of chalcone derivatives via a tandem cross-dehydrogenative-coupling/elimination reaction
  作者：Yu Wei、Jinghua Tang、Xuefeng Cong、Xiaoming Zeng

  DOI：10.1039/c3gc41403e

  日期：——

  Metal-free synthesis of chalcone derivatives through a tandem cross-dehydrogenative-coupling/elimination reaction is described. A simple and inexpensive ammonium persulfate salt enables the reaction between ketones and benzylamines to proceed with high stereoselectivity and good functional group compatibility.

  描述了通过串联的交叉脱氢偶联/消除反应来无金属合成查尔酮衍生物。简单廉价的过硫酸铵盐可使酮与苄胺之间的反应以高的立体选择性和良好的官能团相容性进行。
• Synthesis of Some New Bis[1-(2-aroyl-3-aryl)cyclopropylcarbonyl]benzenes and Pyridines under Phase Transfer Catalysis (PTC) Method
  作者：Dandu Bhaskar Reddy、Biradavolu Seenaiah、Adivireddi Padmaja、Pallela Venkata Ramana Reddy

  DOI：10.1135/cccc19931437

  日期：——

  Some new bis[1-(2-aroyl-3-aryl)cyclopropylcarbonyl]benzenes and pyridines IV - VI have been prepared by the cycloaddition of dimethylsulfonium phenacylide to 1,1'-(1,3-, 1,4-phenylene, and 2,6-pyridylene)-bis(3-aryl-2-propen-1-ones) I - III by adopting two different methods. The advantages of the PTC method over the other have been discussed. The structures of the compound have been confirmed by spectral data.

  一些新的双[1-(2-芳酰基-3-芳基)环丙基羰基]苯和吡啶已通过将二甲基亚砜苯乙炔与1,1'-(1,3-, 1,4-苯基和2,6-吡啶基)-双(3-芳基-2-丙烯-1-酮)进行环加成反应而制备，采用了两种不同的方法。讨论了PTC方法相对于其他方法的优势。该化合物的结构已通过光谱数据确认。
• Rational design, synthesis, and pharmacological characterisation of dicarbonyl curcuminoid analogues with improved stability against lung cancer via ROS and ER stress mediated cell apoptosis and pyroptosis
  作者：Tao Wei、Zhiwei Zheng、Xiaoyan Wei、Yugang Liu、Wentao Li、Bingqing Fang、Di Yun、Zhaojun Dong、Baozhu Yi、Wulan Li、Xiaoping Wu、Dezhi Chen、Liping Chen、Jianzhang Wu

  DOI：10.1080/14756366.2022.2116015

  日期：2022.12.31

  clinical applications. In this article, two types of dicarbonyl curcumin analogues with improved stability were designed through the calculation of molecular stability by density functional theory. Twenty compounds were synthesised, and their anti-tumour activity was screened. A plurality of analogues had significantly stronger activity than curcumin. In particular, compound B2 ((2E,2′E)-3,3′-(1,4-

  摘要 姜黄素是一种具有广泛抗肿瘤活性的天然药物。然而，由于β-二酮部分，姜黄素表现出较差的稳定性和药代动力学，极大地限制了其临床应用。在本文中，通过密度泛函理论计算分子稳定性，设计了两种稳定性得到改善的二羰基姜黄素类似物。合成了二十种化合物，并筛选了它们的抗肿瘤活性。多种类似物的活性明显强于姜黄素。特别是化合物 B2 ((2E,2'E)-3,3'-(1,4-phenylene)bis(1-(2-chlorophenyl)prop-2-en-1-one)) 表现出优异的抗体内和体外肺癌活性. 此外，B2可以上调肺癌细胞中活性氧的水平，进而激活内质网应激，导致细胞凋亡和细胞焦亡。总之，姜黄素类似物 B2 有望成为肺癌治疗的新候选药物，具有改善的化学和生物学特性。
• One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
  作者：Simone Ghinato、Carolina Meazzo、Federica De Nardi、Andrea Maranzana、Marco Blangetti、Cristina Prandi

  DOI：10.1021/acs.orglett.3c01269

  日期：2023.6.2

  A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH2SiMe3 and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediates, which, upon collapse into highly reactive lithium enolates in a solvent-dependent fashion, allows for the assembly of α

  报道了使用 LiCH 2 SiMe 3和羰基化合物作为烯基锂试剂的替代物，对简单的非活化酰胺进行立体选择性烯基化的温和有效的伸缩程序。我们的方法依赖于稳定的四面体中间体的形成，这些中间体在以溶剂依赖性方式分解成高反应性锂烯醇化物后，允许在具有高立体选择性的单一合成操作中组装 α,β-不饱和酮。
• Symmetric Bis-chalcones as a New Type of Breast Cancer Resistance Protein Inhibitors with a Mechanism Different from That of Chromones
  作者：Evelyn Winter、Patrícia Devantier Neuenfeldt、Louise Domeneghini Chiaradia-Delatorre、Charlotte Gauthier、Rosendo Augusto Yunes、Ricardo José Nunes、Tânia Beatriz Creczynski-Pasa、Attilio Di Pietro

  DOI：10.1021/jm401879z

  日期：2014.4.10

  Potent ABCG2 inhibitors were recently identified as asymmetric chromones with different types of substituents. We here synthesized symmetric bis-chalcones that were differently substituted and screened for their ability to inhibit mitoxantrone efflux from ABCG2-transfected HEK293 cells. Potent bis-chalcone inhibitors were identified, the efficiency depending on both position of the central ketone groups and the number and positions of lateral methoxy substituents. The best derivative, namely, 1p, was selective for ABCG2 over P-glycoprotein and MRP1, appeared not to be transported by ABCG2, and was at least as active on various drug-selected cancer cells overexpressing ABCG2. Compound 1p stimulated the ABCG2 basal ATPase activity by contrast to a chromone lead that inhibited it, suggesting different mechanisms of interaction. Combination of both types of inhibitors produced synergistic effects, leading to complete inhibition at very low