trans-styryl(2',3',4',5',6'-pentafluorophenyl)ketone | 54081-33-3

• 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: trans-styryl(2',3',4',5',6'-pentafluorophenyl)ketone
• 英文别名: (E)-1-(perfluorophenyl)-3-phenylprop-2-en-1-one；1-(pentafluorophenyl)-3-phenylprop-2-en-1-one；1-pentafluorophenyl-3-phenylprop-2-en-1-one；1-pentafluorophenyl-3-phenylpropen-1-one；(E)-1-(2,3,4,5,6-pentafluorophenyl)-3-phenylprop-2-en-1-one
• CAS: 54081-33-3
• 化学式: C₁₅H₇F₅O
• 分子量: 298.212
• InChiKey: LBHOSKBIBWDCFT-VOTSOKGWSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  377.9±42.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 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：
  6

反应信息

• 作为反应物：
  描述：

  trans-styryl(2',3',4',5',6'-pentafluorophenyl)ketone 在 盐酸胍 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 肉桂酸
  参考文献：
  名称：

  Reaction of polyfluorinated chalcones with guanidine

  摘要：

  Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.

  DOI：

  10.1134/s1070428015120143
• 作为产物：
  描述：

  溴五氟苯 在 2,6-二甲基吡啶 、 戴斯-马丁氧化剂 、 magnesium 、 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 trans-styryl(2',3',4',5',6'-pentafluorophenyl)ketone
  参考文献：
  名称：

  使用可回收的氧铵盐脱氢全氟烷基酮

  摘要：

  描述了全氟烷基酮通过氧代铵盐 4-乙酰氨基-2,2,6,6-四甲基哌啶-1-四氟硼酸氧代铵（4-NHAc-TEMPO+BF4–，博比特盐，1）进行的新型脱氢反应。该反应在弱碱性条件下进行，似乎是全氟烷基酮所独有的。给出了这种不寻常转换的建议机制。反应的副产物 4-乙酰氨基-2,2,6,6-四甲基-1-哌啶基氧基 (1a) 可以很容易地回收并用于再生氧铵盐。

  DOI：

  10.1002/ejoc.201300392

文献信息

• Synthesis and biological evaluation of aromatic enones related to curcumin
  作者：Thomas Philip Robinson、Richard B. Hubbard、Tedman J. Ehlers、Jack L. Arbiser、David J. Goldsmith、J. Phillip Bowen

  DOI：10.1016/j.bmc.2005.03.054

  日期：2005.6

  It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or

  姜黄素是从香料姜黄中分离得到的天然产物，已显示出广泛的药理活性，包括某些抗癌特性。它已被明确地证明是在体外和体内血管生成的有效抑制剂。使用姜黄素作为抗血管生成类似物设计的先导化合物，已经合成了一系列利用取代的查尔酮骨架的结构相关化合物，并通过已建立的SVR细胞增殖测定法进行了测试。结果产生了范围广泛的化合物，这些化合物等于或超过姜黄素体外抑制内皮细胞生长的能力。由于它们的商业可获得性和相当简单的合成制备方法，这些低分子量化合物是开发未来血管生成抑制剂的诱人线索。
• Chiral octahedral complexes of Co(<scp>iii</scp>) as catalysts for asymmetric epoxidation of chalcones under phase transfer conditions
  作者：Vladimir A. Larionov、Elina P. Markelova、Alexander F. Smol'yakov、Tat'yana F. Savel'yeva、Victor I. Maleev、Yuri N. Belokon

  DOI：10.1039/c5ra11760g

  日期：——

  Stereochemically inert and positively charged chiral complexes of Co(III) were shown to catalyze the asymmetric epoxidation of chalcones with H2O2 under phase transfer conditions. The reaction products had enantiomeric purities of up to 55%. It was also shown that complex 1a I− catalyzed the coupling reaction of a resulting epoxide with CO2 (conversion 72%).

  在相转移条件下，Co（III）的立体化学惰性和带正电荷的手性配合物可催化查耳酮与H 2 O 2的不对称环氧化。反应产物的对映体纯度高达55％。它也表明，复杂1A我-催化的与CO所得环氧化物的偶联反应2（转化72％）。
• 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。
• Syntheses and UV-visible spectroscopic properties of new ‘fluorophilic’ fluorine- and perfluoroalkyl-substituted solvatochromic pyridinium<i>N</i>-phenolate betaine dyes
  作者：Christian Reichardt、Michael Eschner、Gerhard Schäfer

  DOI：10.1002/poc.427

  日期：2001.11

  Syntheses and negative solvatochromism of three new ‘fluorophilic’ fluorine- and perfluoroalkyl-substituted pyridinium N-phenolate betaine dyes 3–5 are described in order to obtain new zwitterionic dyes which should be less basic and better soluble in perfluorinated solvents than the solvatochromic standard betaine dyes 1 and 2, used to establish an empirical scale of solvent polarity, called the ET

  合成及负溶致变色三个新的“亲氟”含氟和全氟烷基-取代的吡啶鎓ñ -苯酚甜菜碱染料3 - 5，以获得新的两性离子染料应该是碱性较弱的和在除溶剂化标准甜菜碱全氟化溶剂可溶性更好地描述染料1和2用于建立溶剂极性的经验标度，称为E T（30）或标度。新的甜菜碱染料3 - 5被设计成允许现有的延伸ë Ť（30）以适应新的溶剂。版权所有©2001 John Wiley＆Sons，Ltd.
• Aryl Palladium Carbene Complexes and Carbene-Aryl Coupling Reactions
  作者：Ana C. Albéniz、Pablo Espinet、Raúl Manrique、Alberto Pérez-Mateo

  DOI：10.1002/chem.200400811

  日期：2005.2.18

  moiety from [W(CO)5C(NEt2)R}] to palladium leads to isolable monoaminocarbene palladium aryl complexes [Pd(mu-Br)Pf[C(NEt2)R]}2] (R = Me, Ph; Pf = C6F5). When [W(CO)5C(OMe)R}] is used, the corresponding palladium carbenes cannot be isolated since these putative, more electrophilic carbenes undergo a fast migratory insertion process to give alkyl palladium complexes. These complexes could be stabilized

  氨基碳烯基团从[W（CO）5 C（NEt2）R}]过渡金属到钯导致可分离的单氨基碳烯钯芳基配合物[Pd（mu-Br）Pf [C（NEt2）R]} 2]（R = Me，Ph; Pf = C6F5）。当使用[W（CO）5 C（OMe）R}]时，不能分离出相应的钯碳烯，因为这些推定的，更多的亲电子碳烯会经历快速迁移插入过程，从而生成烷基钯络合物。对于R = 2-苯基乙烯基，这些络合物可以以eta3-烯丙基形式稳定；对于R = Ph，可以以较不稳定的eta3-苄基形式存在。水解产物和五氟苯基乙烯基甲基醚（当R = Me时）也被观察到。单氨基卡宾通过卡宾-芳基偶联缓慢分解，生成相应的亚胺盐，并根据反应条件，生成相应的水解产物。卡宾碳的亲电性主要由杂原子基团的性质决定，它通过卡宾-芳基偶合控制了析出的难易程度。因此，对于二氨基卡宾钯芳基络合物没有观察到卡宾-芳基偶联。