1,4-bis-(3-oxo-3-phenyl-propenyl)-benzene | 3251-38-5

• 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
• 英文名称: 1,4-bis-(3-oxo-3-phenyl-propenyl)-benzene
• 英文别名: Terephthalbis(acetophenone)；1,4-Bis-<β-benzoyl-vinyl>benzol；1,4-Bis-<3-oxo-3-phenyl-propen-(1)-yl>benzol；1,4-Di-(benzoylvinyl)-benzol；Terephthalacetophenon；3,3'-p-Phenylen-di-<1-phenyl-prop-2-en-1-on>；1,4-Bis-(3-oxo-3-phenyl-propenyl)-benzol；1,4-Di(3-oxo-3-phenylprop-1-enyl)benzol；Terephthalylidendibenzoyl；p-Isodichalcon；1.4-Bis-(β-benzoyl-vinyl)-benzol；Terephthalylidendiacetophenon；2-Propen-1-one, 3,3'-(1,4-phenylene)bis[1-phenyl-；3-[4-(3-oxo-3-phenylprop-1-enyl)phenyl]-1-phenylprop-2-en-1-one
• CAS: 3251-38-5
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: ISDFLLZGOWAGAF-UHFFFAOYSA-N

物化性质

• 熔点：
  201 °C
• 沸点：
  537.8±50.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

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：

  1,4-bis-(3-oxo-3-phenyl-propenyl)-benzene 在 一水合肼 作用下， 以 乙醇 为溶剂， 以82%的产率得到3-phenyl-5-[4-(3-phenyl-2-pyrazolin-5-yl)phenyl]-2-pyrazoline
  参考文献：
  名称：

  杂环。7.合成新的吡唑啉

  摘要：

  DOI：

  10.1021/je00042a042
• 作为产物：
  描述：

  1,4-bis-(1-chloro-3-oxo-3-phenyl-propyl)-benzene 生成 1,4-bis-(3-oxo-3-phenyl-propenyl)-benzene
  参考文献：
  名称：

  v. Lendenfeld, Monatshefte fur Chemie, 1906, vol. 27, p. 971

  摘要：

  DOI：

文献信息

• Chiral Aldehyde Catalysis for the Catalytic Asymmetric Activation of Glycine Esters
  作者：Wei Wen、Lei Chen、Ming-Jing Luo、Yan Zhang、Ying-Chun Chen、Qin Ouyang、Qi-Xiang Guo

  DOI：10.1021/jacs.8b06676

  日期：2018.8.1

  Chiral aldehyde catalysis is uniquely suitable for the direct asymmetric α-functionalization of N-unprotected amino acids, because aldehydes can reversibly form imines. However, there have been few successful reports of these transformations. In fact, only chiral aldehyde catalyzed aldol reactions of amino acids and alkylation of 2-amino malonates have been reported with good chiral induction. Here

  手性醛催化特别适用于 N-未保护氨基酸的直接不对称 α-官能化，因为醛可以可逆地形成亚胺。然而，关于这些转变的成功报道很少。事实上，只有手性醛催化氨基酸的羟醛反应和 2-氨基丙二酸酯的烷基化具有良好的手性诱导作用。在这里，我们报告了一种基于烯醇中间体表面控制的新型手性醛催化剂。由此产生的手性醛是第一种有效的非吡哆醛依赖性催化剂，可以促进 N-未保护甘氨酸酯的直接不对称 α-官能化。通过密度泛函理论计算研究了可能的过渡态和质子转移过程。
• Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica
  作者：Abdul R. Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.11.005

  日期：2009.1

  condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica

  在碱性条件下，用N-4取代的硫代氨基脲将查尔酮环化，导致形成新的化合物硫代氨基甲酰基双吡唑啉衍生物。通过UV，IR，1 H NMR，13 C NMR和ESI-MS光谱数据以及热重分析阐明了化合物的结构，并通过元素分析证实了其纯度。这些复合物的antiamoebic活性通过对微量稀释法评估HM1：IMSS的应变阿米巴并将结果与​​标准药物甲硝唑进行比较。结构-活性关系表明，在硫代氨基甲酰基上具有芳香取代基的化合物比具有环状基团的化合物更具活性。但是，从IC 50值可以清楚地看出，化合物15和20具有更高的活性，并且两者都显示出结构相似性，其中吸电子基团连接在苯环上。MTT分析表明所有化合物对人肾上皮细胞系无毒。
• Aluminum chloride–catalyzed C-alkylation of pyrrole and indole with chalcone and bis-chalcone derivatives
  作者：Meliha Burcu Gürdere、Oguz Özbek、Mustafa Ceylan

  DOI：10.1080/00397911.2015.1136644

  日期：2016.2.16

  AlCl3-catalyzed alkylation of pyrrole (2) with chalcone (1a–i) at a ratio of 8:1 in the presence of 10 mol% AlCl3 gave the solely 2-alkyl pyrroles (3a–i) at room temperature for 12 in good yields. The same reaction was performed with pyrrole (2) and chalcone at a ratio of 1:3 in CH3CN at rt for 3 h to achieve 2,5-dialkyl pyrroles (4a–f). In addition, the reaction of the pyrrole (2) and indole (7) on 1,4-phenylene

  摘要 AlCl3 催化吡咯 (2) 与查耳酮 (1a-i) 以 8:1 的比例在 10 mol% 存在下烷基化，在室温下得到单独的 2-烷基吡咯 (3a-i) 12收益良好。使用比例为 1:3 的吡咯 (2) 和查耳酮在 CH3CN 中在室温下进行相同的反应 3 小时，以获得 2,5-二烷基吡咯 (4a-f)。此外，吡咯 (2) 和吲哚 (7) 在 1,4-亚苯基双查耳酮 (5a-g) 上以 8:1 的比例在室温下反应 24 小时，得到双加成产物 6a- g 和 8a-g 分别具有良好的产量。产物的结构经1H和13C核磁共振谱和元素分析证实。图形概要
• Synthesis and in vitro anticancer evaluation of 1,4-phenylene-bis-pyrimidine-2-amine derivatives
  作者：Meliha Burcu GÜRDERE、Erdoğan KAMO、Ayşe ŞAHİN YAĞLIOĞLU、Yakup BUDAK、Mustafa CEYLAN

  DOI：10.3906/kim-1603-112

  日期：——

  A series of 1,4-phenylene-bis-chalcones 3a-3h were synthesized by the reaction of terephthalaldehyde with substituted arylketones in this study. The novel 1,4-phenylene-bis-pyrimidine-2-amine derivatives 5a-5h were obtained by the addition of guanidine hydrochloride to 1,4-phenylene-bis-chalcone 3a-3h in ethanolic KOH under reflux conditions. The structure of the compounds was explained by means of IR, $^1}$H NMR, $^13}$C NMR, and elemental analyses. The anticancer activities of 3a-3h and 5a-5h were investigated against rat brain tumor cells and human uterus carcinoma in vitro$.$ Activity tests were performed as dose-dependent assays at eight concentrations. The positive control was 5-fluorouracil (5-FU). Compounds 3c and 3d were examined and they showed high activities as compared to 5-FU against C6 (rat brain tumor) and HeLa (human uterus carcinoma) cells. The anticancer activity of 5h was better than that of 5-FU at high concentrations cell-selectively against C6 cells.

  在本研究中，通过邻苯二甲醛与取代芳基酮的反应合成了系列1,4-亚苯基双查尔酮3a-3h。在回流条件下，将盐酸胍加入到1,4-亚苯基双查尔酮3a-3h中，在乙醇钾溶液中得到了新型1,4-亚苯基双嘧啶-2-胺衍生物5a-5h。通过红外光谱、核磁共振（1H NMR和13C NMR）及元素分析解释了化合物的结构。对3a-3h和5a-5h的抗癌活性进行了研究，针对大鼠脑肿瘤细胞和人子宫颈癌在体外进行了活性测试，活性测试以剂量依赖性方式在八种浓度下进行。阳性对照为5-氟尿嘧啶（5-FU）。经过检测，化合物3c和3d显示出相较于5-FU对C6（大鼠脑肿瘤）和HeLa（人子宫颈癌）细胞的高活性。在高浓度下，5h对C6细胞的选择性抗癌活性优于5-FU。
• ‘One-pot’ ultrasound irradiation promoted synthesis and spectral characterization of an array of novel 1,1′-(5,5′-(1,4-phenylene)bis(3-aryl-1H-pyrazole-5,1(4H,5H)-diyl))diethanones, a bis acetylated pyrazoles derivatives
  作者：V. Kanagarajan、M.R. Ezhilarasi、M. Gopalakrishnan

  DOI：10.1016/j.saa.2010.11.038

  日期：2011.2

  An array of novel 1,1'-(5,5'-(1,4-phenylene)bis(3-aryl-1H-pyrazole-5,1(4H,5H)-diyl))diethanones, a bis acetylated pyrazoles derivatives are synthesized in 'one-pot' by ultrasound irradiation method and are characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (1H and 13C) and two-dimensional NOESY spectra. The methylene and methane protons of pyrazoles moiety splits signal

  一系列新型1,1'-（5,5'-（1,4-亚苯基）双（3-芳基-1H-吡唑-5,1（4H，5H）-二基））二酮，双乙酰化吡唑衍生物通过超声辐射法在“一锅法”中合成，并通过熔点，元素分析，MS，FT-IR，一维NMR（1H和13C）和二维NOESY光谱进行表征。吡唑部分的亚甲基和甲烷质子在质子NMR光谱中以ABX模式分裂信号，NOESY光谱证实了关键的nOe相关性。