(E)-1-(2,4-difluorophenyl)-3-phenylprop-2-en-1-one

• 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: (E)-1-(2,4-difluorophenyl)-3-phenylprop-2-en-1-one
• 化学式: C₁₅H₁₀F₂O
• 分子量: 244.241
• InChiKey: GOKXZCOISYHMMK-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,4-difluorophenyl)-3-phenylprop-2-en-1-one 在 palladium on activated charcoal 甲酸 、 三正丁胺 作用下， 反应 10.0h， 生成 1-(2,4-二氟苯基)-3-苯基-1-丙酮
  参考文献：
  名称：

  Karki, Rajeshri G.; Gokhale, Vijay M.; Kharkar, Prashant S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 372 - 381

  摘要：

  DOI：
• 作为产物：
  描述：

  2',4'-二氟苯乙酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以76%的产率得到(E)-1-(2,4-difluorophenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Predicting the photoinduced electron transfer thermodynamics in polyfluorinated 1,3,5-triarylpyrazolines based on multiple linear free energy relationships

  摘要：

  1,3,5-三芳基吡唑啉的光物理特性受到附着在芳环上的取代基的性质和位置的强烈影响，使得这一荧光基团平台非常适合设计利用光诱导电子转移（PET）开关机制的荧光探针。为了探索控制PET热力学的两个关键参数的可调性，即激发态能量ΔE00和受体电势E(A/A−)，研究人员合成并表征了一系列多氟取代的1,3-二芳基-5-苯基-吡唑啉。通过对每个芳环使用一组独立的取代基常数，观察到的PET参数趋势可以通过多个Hammett线性自由能关系（LFER）有效捕捉。由于缺乏多氟取代芳香族化合物的实验Hammett常数，研究人员使用基于碳原子核电势（EPN）理论推导出的常数作为量子化学描述符。用一组不包括在训练集中的化合物评估LFER的性能，预测的结合PET参数的平均无符号误差为0.05 eV。所述的LFER方法非常适合设计和优化阳离子响应的1,3,5-三芳基吡唑啉的性能。

  DOI：

  10.1039/b821042j

文献信息

• Predicting the photoinduced electron transfer thermodynamics in polyfluorinated 1,3,5-triarylpyrazolines based on multiple linear free energy relationships
  作者：Manjusha Verma、Aneese F. Chaudhry、Christoph J. Fahrni

  DOI：10.1039/b821042j

  日期：——

  The photophysical properties of 1,3,5-triarylpyrazolines are strongly influenced by the nature and position of substituents attached to the aryl-rings, rendering this fluorophore platform well suited for the design of fluorescent probes utilizing a photoinduced electron transfer (PET) switching mechanism. To explore the tunability of two key parameters that govern the PET thermodynamics, the excited state energy ΔE00 and the acceptor potential E(A/A−), a library of polyfluoro-substituted 1,3-diaryl-5-phenyl-pyrazolines was synthesized and characterized. The observed trends for the PET parameters were effectively captured through multiple Hammett linear free energy relationships (LFER) using a set of independent substituent constants for each of the two aryl rings. Given the lack of experimental Hammett constants for polyfluoro-substituted aromatics, theoretically derived constants based on the electrostatic potential at the nucleus (EPN) of carbon atoms were employed as quantum chemical descriptors. The performance of the LFER was evaluated with a set of compounds that were not included in the training set, yielding a mean unsigned error of 0.05 eV for the prediction of the combined PET parameters. The outlined LFER approach should be well suited for designing and optimizing the performance of cation-responsive 1,3,5-triarylpyrazolines.

  1,3,5-三芳基吡唑啉的光物理特性受到附着在芳环上的取代基的性质和位置的强烈影响，使得这一荧光基团平台非常适合设计利用光诱导电子转移（PET）开关机制的荧光探针。为了探索控制PET热力学的两个关键参数的可调性，即激发态能量ΔE00和受体电势E(A/A−)，研究人员合成并表征了一系列多氟取代的1,3-二芳基-5-苯基-吡唑啉。通过对每个芳环使用一组独立的取代基常数，观察到的PET参数趋势可以通过多个Hammett线性自由能关系（LFER）有效捕捉。由于缺乏多氟取代芳香族化合物的实验Hammett常数，研究人员使用基于碳原子核电势（EPN）理论推导出的常数作为量子化学描述符。用一组不包括在训练集中的化合物评估LFER的性能，预测的结合PET参数的平均无符号误差为0.05 eV。所述的LFER方法非常适合设计和优化阳离子响应的1,3,5-三芳基吡唑啉的性能。
• Ligand-Free Palladium-Catalyzed Substoichiometric Base ­Mediated Carbonylation of Aryl Iodides with Alkenylboronic Acids under Ambient Conditions
  作者：Lili Tang、Yanqun Gao、Yuejun Ouyang、Wei Han、Junjie Chen、Linlin Yang、Bing Xiao、Ge Shen

  DOI：10.1055/a-2007-2958

  日期：——

  A highly efficient, practical, and ligand-free palladium-catalyzed carbonylation of aryl iodides with alkenylboronic acids has been developed. A variety of chalcones and α-branched enones were isolated in satisfactory to good yields with good substrate compatibilities under an ambient pressure of CO at room temperature. Moreover, the transformation proceeds well in the presence of a substoichiometric

  开发了一种高效、实用且无配体的钯催化芳基碘与烯基硼酸的羰基化反应。在室温和 CO2 环境压力下，各种查尔酮和 α-支链烯酮的分离结果令人满意，产率良好，底物相容性好。此外，在存在亚化学计量量的碱的情况下，转化进行得很好。该策略作为后期功能化平台的优点已通过对源自雌酮和 3-苯基- 的复杂底物的修饰得到证明升-丙氨酸。
• Mechanochemical Assisted Chemoselective and Stereoselective Hydrogen‐Bonding Catalyzed Addition of Dithiomalonates to Enones
  作者：Żaneta A. Mała、Mikołaj J. Janicki、Robert W. Góra、Krzysztof A. Konieczny、Rafał Kowalczyk

  DOI：10.1002/adsc.202300636

  日期：2023.10.13

  be active nucleophiles in the stereoselective additions to chalcones, dienones, and en-ynones affording the desired Michael adducts with moderate to good yield and enantioselectivities up to 98%. In contrast, the analogous dibenzyl malonate remained inactive. Bifunctional Cinchona squaramides secured the effective chirality transfer and the selectivity towards Michael adducts of various bisthiomalonates

  事实证明，二硫代丙二酸酯在查尔酮、二烯酮和烯炔酮的立体选择性加成中是活性亲核试剂，可提供所需的迈克尔加合物，产率中等至良好，对映选择性高达 98%。相反，类似的丙二酸二苄酯仍然没有活性。双功能金鸡纳方酰胺确保了有效的手性转移以及按照软烯醇化方法对各种双硫代丙二酸酯的迈克尔加合物的选择性。硫酯的性质影响反应物或产物的反应性和稳定性。在溶液中进行的反应产生了产物，但需要较长的时间以及磺胺-迈克尔加合物等副产物的形成，从而限制了更具反应性的二硫酯的应用。相反，在无溶剂、球磨条件下进行的反应在显着更短的时间内提供加合物，并且副产物的产生可以忽略不计或没有。因此，机械化学方法被证明是支持标准溶液条件下难以有效反应的有效工具。进行的全面 KS-DFT 研究与实验观察结果一致，更多地揭示了分子水平上复杂的活性亲核试剂的形成和不同的化学反应途径，并表明了控制观察到的立体选择性的关键过渡态。
• Karki, Rajeshri G.; Gokhale, Vijay M.; Kharkar, Prashant S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 372 - 381
  作者：Karki, Rajeshri G.、Gokhale, Vijay M.、Kharkar, Prashant S.、Kulkarni, Vithal M.

  DOI：——

  日期：——
• Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity
  作者：Saeed Attar、Zachary O’Brien、Hasan Alhaddad、Melissa L. Golden、Alejandro Calderón-Urrea

  DOI：10.1016/j.bmc.2011.01.048

  日期：2011.3

  A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy (H-1 NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10(-4) M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity. Published by Elsevier Ltd.