(E)-1-(4-methylphenyl)-3-{(4-(trifluoromethyl)phenyl)}-2-propen-1-one | 1004651-40-4

• 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-(4-methylphenyl)-3-{(4-(trifluoromethyl)phenyl)}-2-propen-1-one
• 英文别名: (E)-1-p-tolyl-3-(4-trifluoromethylphenyl)propenone；(E)-1-(4-methylphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1004651-40-4
• 化学式: C₁₇H₁₃F₃O
• 分子量: 290.285
• InChiKey: UUPKTZDIXRHGTQ-IZZDOVSWSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  374.0±42.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methylphenyl)-3-{(4-(trifluoromethyl)phenyl)}-2-propen-1-one 在 sodium tetrahydroborate 、 1,10-菲罗啉 、 cerium(III) chloride heptahydrate 、 sodium t-butanolate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 1-(p-tolyl)-3-(4-(trifluoromethyl)phenyl)propan-1-one
  参考文献：
  名称：

  Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

  摘要：

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

  DOI：

  10.1021/acs.orglett.5b03124
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 对甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(4-methylphenyl)-3-{(4-(trifluoromethyl)phenyl)}-2-propen-1-one
  参考文献：
  名称：

  Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

  摘要：

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

  DOI：

  10.1021/acs.orglett.5b03124

文献信息

• Copper-catalyzed oxidative cyclization of chalcone and benzylic amine leading to 2,5-diaryl oxazoles via carbon–carbon double bond cleavage
  作者：Dongfang Liu、Jintao Yu、Jiang Cheng

  DOI：10.1016/j.tet.2013.12.077

  日期：2014.2

  oxidative cyclization of chalcone with benzylic amine is achieved, providing 2,5-diaryl oxazoles in moderate to good yields. The procedure employs O2 as a clean oxidant and involves an oxidative cleavage of the CC bond as the key step.

  实现了查尔酮与苄基胺的铜催化氧化环化，以中等至良好的产率提供了2,5-二芳基恶唑。该方法使用O 2作为清洁氧化剂，并且涉及C C键的氧化裂解作为关键步骤。
• Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: efficient synthetic methods for diaryl ketones and chalcones at room temperature
  作者：Daisuke Ogawa、Keita Hyodo、Masato Suetsugu、Jing Li、Yoshiaki Inoue、Mamoru Fujisawa、Masayuki Iwasaki、Kentaro Takagi、Yasushi Nishihara

  DOI：10.1016/j.tet.2013.01.058

  日期：2013.3

  Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or chalcones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing

  在噻吩-2-羧酸铜（I）作为活化剂的条件下，在室温下在严格的非碱性条件下，在钯中，芳基或烯基硼酸与酰基氯的钯催化交叉偶联反应得到二芳基酮或查耳酮，产率中等至优异。在芳族环上带有给电子或吸电子取代基的多种基材是相容的。
• Asymmetric Conjugate Addition of Phosphonates to Enones Using Cinchona–Diaminomethylenemalononitrile Organocatalysts
  作者：Ryoga Arai、Shin-ichi Hirashima、Tatsuki Nakano、Masahiro Kawada、Hiroshi Akutsu、Kosuke Nakashima、Tsuyoshi Miura

  DOI：10.1021/acs.joc.9b02553

  日期：2020.3.6

  Asymmetric conjugate additions of phosphonates to trans-crotonophenone and chalcone derivatives using a diaminomethylenemalononitrile organocatalyst resulted in the generation of the corresponding chiral γ-ketophosphonates in high yields with excellent enantioselectivities (up to 95% ee). This report is the first successful example of asymmetric 1,4-additions of phosphonate to α,β-unsaturated ketones

  使用二氨基亚甲基丙二腈有机催化剂将膦酸酯不对称共轭添加到反式巴豆酮和查尔酮衍生物中，可以以高收率生成具有出色对映选择性（最高95％ee）的相应手性γ-酮膦酸酯。该报告是使用有机催化剂将膦酸酯不对称地与α，β-不饱和酮进行1,4-加成的第一个成功实例。
• 1-(4-Methane(amino)sulfonylphenyl)-3-(4-substituted-phenyl)-5-(4-trifluoromethylphenyl)-1H-2-pyrazolines/pyrazoles as potential anti-inflammatory agents
  作者：Khaled R.A. Abdellatif、Heba A.H. Elshemy、Amany A. Azoz

  DOI：10.1016/j.bioorg.2015.09.002

  日期：2015.12

  2-Pyrazolins 14a-l and pyrazoles 15a-l were designed as celecoxib analogs for the evaluation of their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. Compounds 14i, 15a, 15d and 15f were the most COX-2 selective derivatives (S.I. = 5.93, 6.08, 5.03 and 5.27 respectively) while the pyrazoline derivatives 14g and 14i exhibited the highest AI activity (ED50 = 190.5 and 160.1 mu mol/kg po, respectively). (C) 2015 Elsevier Inc. All rights reserved.
• NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER
  申请人：Neckers Jane B.

  公开号：US20140171503A1

  公开（公告）日：2014-06-19

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R 1 to R 5 and X 1 to X 5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.