3-(anthracen-10-yl)-1-(4-methoxyphenyl)prop-2-en-1-one | 88483-90-3

• 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: 3-(anthracen-10-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 3-(anthracen-9-yl)-1-(4-methoxyphenyl)prop-2-en-1-one；3-(9-anthryl)-1-(4-methoxyphenyl)-2-propen-1-one；AMPO；2-Propen-1-one, 3-(9-anthracenyl)-1-(4-methoxyphenyl)-；3-anthracen-9-yl-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 88483-90-3
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: DEGUZIIIXRXDKA-UHFFFAOYSA-N

物化性质

• 熔点：
  107.4 °C(Solv: methanol (67-56-1))
• 沸点：
  566.5±50.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(anthracen-10-yl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以81.4%的产率得到3-anthracen-9-yl-5-(4-methoxy-phenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  3,5-二取代4,5-二氢-1H-吡唑含氮杂环衍生物的简便一锅法合成方法及其生物学评价和分子对接研究

  摘要：

  一系列 2-吡唑啉衍生物（PS-1 到 PS-16）是通过不同的芳香/杂芳香醛和酮反应合成的，在两步反应中通过克莱森-施密特缩合反应，然后将所得查尔酮与水合肼环化使用常规方法和微波方法在碱存在的情况下。合成的衍生物通过各种物理化学方法进行表征，包括 IR、1H-NMR、13C-NMR、质谱数据和元素分析。使用合适的动物模型评估抗抑郁和抗焦虑活性。化合物 PS-3 和 PS-14 显示出显着的抗抑郁活性，通过在两个测试中减少不动的持续时间，同时发现化合物 PS-9 和 PS-12 在测试剂量（50 和 100 毫克/千克体重）下与标准药物丙咪嗪和丙咪嗪相比具有良好的抗焦虑活性（通过增加手臂进入次数和开放手臂探索时间）地西泮，分别。为了阐明合成衍生物与 MAO-A 靶蛋白的结合相互作用，采用了分子对接，证明了与结合位点处的氨基酸残基 Phe208、Asn181 和 Tyr407 的关键相互作用。此外，预测合成衍生物的

  DOI：

  10.1007/s11094-017-1655-7
• 作为产物：
  描述：

  9-蒽甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-(anthracen-10-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Tuning Solid-State Fluorescence of a Twisted π-Conjugated Molecule by Regulating the Arrangement of Anthracene Fluorophores

  摘要：

  1-(5-(Anthracen-9-yl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl)ethanone was synthesized and crystallized to provide three types of crystals with different fluorescent colors and host-guest structures. Crystal structure analysis reveals that this compound possesses twisted pi-conjugated structure and different degrees of distortion depending on guest molecules in the three crystal structures. The anthracene fluorophore stacking modes are regulated from monomer arrangement to face-to-face pi-stacked arrangement by means of the entrapment of organic acid molecules in the lattice. The vibrational spectroscopy, thermal behaviors, diffuse reflectance absorption spectroscopy, solid-state fluorescence properties, and fluorescence quantum yields and lifetimes of the three types of crystals were investigated. Such properties are closely related to the fluorophore stacking modes and intermolecular electronic interactions in crystals. The pi-stacked geometries of anthracene fluorophores are responsible for the red-shifted emissions and longer fluorescence lifetimes. It indicates that the optical properties of organic materials could be modulated by entrapping different guest molecules in lattice.

  DOI：

  10.1021/cg301055j

文献信息

• Understanding relationship between stacking modes and optical properties of organic charge transfer cocrystals involving anthracyl chalcones and TCNB
  作者：Hao Sun、Arshad Khan、Rabia Usman、Mingliang Wang

  DOI：10.1016/j.jphotochem.2018.11.019

  日期：2019.2

  5-tetracyanobenzene (TCNB) as electron acceptor. Crystal structure analysis demonstrates that two types of face-to-face patterns (D···A···D···A···D and DAD···DAD) were mainly formed via π···π interactions. X-ray diffraction, vibration spectroscopy, thermal behaviors, solid-state absorption spectroscopy and fluorescence properties were employed to assess the relations between their structures and performance

  通过自组装过程获得了四个摩尔比不同的电荷转移（CT）共晶体，涉及3-（9-蒽基）-1-苯基-2-丙-1-酮（APPO），3-（9-蒽基） -1-（4-甲氧基苯基）-2-丙-1-酮（AMPO），3-（9蒽基）-1-（1-萘基）-2-丙-1-酮（ANPO）作为电子供体和1,2,4,5-四氰基苯（TCNB）作为电子受体。晶体结构分析表明，两种类型的面对面图案（D···A···D···A··D和DAD···DAD）主要是通过π··π相互作用形成的。利用X射线衍射，振动光谱，热行为，固态吸收光谱和荧光性质来评估其结构与性能之间的关系。值得注意的是，相对于原始供体，共晶体的荧光特性显示出明显的增加，这是由于供体和受体分子之间的电荷转移相互作用引起的。这些结果显然有助于更好地认识CT共晶体中的堆叠模式与光学性质之间的关系。
• Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation
  作者：Yan Zhu、Jia Liu、Meiheng Lv、Tingting Wang、Dongxiang Zhang、Rong Shang、Xin-Dong Jiang、Jianjun Du、Guiling Wang

  DOI：10.1016/j.cclet.2023.109446

  日期：2023.12

  effect and improve the generation efficiency of reactive oxygen species (ROS). Since orthogonal molecular orbitals of donor-acceptor (D-A) pairs favor the SOCT-ISC transition, herein aza-borondipyrromethenes (aza-BODIPYs) with 1,7-di-anthracyl groups (An-azaBDP) was successfully prepared, owing to steric hindrance to produce a big dihedral angle between the two molecular orbital (MO) planes. Moreover

  自旋轨道电荷转移系间窜越（SOCT-ISC）可以直接克服传统重原子效应的缺点，提高活性氧（ROS）的生成效率。由于供体-受体（D-A）对的正交分子轨道有利于SOCT-ISC转变，因此由于空间位阻，成功制备了具有1,7-二蒽基基团（An-azaBDP）的氮杂硼二吡咯亚甲基（aza-BODIPYs）在两个分子轨道（MO）平面之间产生大的二面角。此外，根据密度泛函理论（DFT）和瞬态密度泛函理论（TDDFT），An-azaBDP的S-T轨道之间的能量差很小，并且更倾向于ISC。 An-azaBDP在光照射下能有效产生单线态氧。 An-azaBDP 光照射可诱导 SW620 细胞凋亡，可作为治疗癌细胞和肿瘤的潜在候选者。
• Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation
  作者：Nibha Mishra、D. Sasmal

  DOI：10.1016/j.bmcl.2011.02.030

  日期：2011.4

  In an effort to develop selective MAO (monoamine oxidase) B inhibitors, structure based virtual screening was initiated on an in-house library. Top 10 HITS were synthesized and evaluated for MAO (A and B) inhibitory activity, both against human and rat enzymes. All the compounds were found selective, reversible and active in nM range (100 times more potent than selegeline) towards MAO-B. Outstanding co-relation between predicted and experimental K(i) values were observed. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and bioactivity of chalcones and its analogues
  作者：Chao Niu、Adila Tuerxuntayi、Gen Li、Madina Kabas、Chang-Zhi Dong、Haji Akber Aisa

  DOI：10.1016/j.cclet.2017.03.018

  日期：2017.7

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Synthesis and thermal decomposition of 3-aroyl-4-aryl-2-pyrazolines
  作者：A. L�vai

  DOI：10.1007/bf00824303

  日期：1995.11

  3-Aroyl-4-aryl-2-pyrazolines (21-40) have been synthesized by the reaction of alpha,beta-unsaturated ketones (1-20) with diazomethane. These 2-pyrazolines gave beta-methyl-alpha,beta-unsaturated ketones (41-46) on thermal denitrogenation.