(E)-2-methyl-3-(4-nitrophenyl)-1-phenyl-2-propen-1-one | 67615-54-7

• 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)-2-methyl-3-(4-nitrophenyl)-1-phenyl-2-propen-1-one
• 英文别名: (E)-2-methyl-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one
• CAS: 67615-54-7
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: HONRMHJBJQRDGO-VAWYXSNFSA-N

物化性质

• 沸点：
  404.7±37.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-(4-nitrophenyl)-1-phenyl-2-propen-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 以134 mg的产率得到(2E)-2-methyl-3-(4-nitrophenyl)-1-phenylprop-2-en-1-ol
  参考文献：
  名称：

  取代基对1,3-二芳基烯丙基阳离子形成高取代茚基的4π-电环选择性的影响

  摘要：

  在路易斯酸存在下通过电离相应的烯丙醇而生成的差异取代的1,3-二芳基取代的烯丙基阳离子经历化学选择性和区域选择性电环化反应以生成1-芳基-1 H-茚。仅具有2-取代基且2-酯和2-烷基取代基均被耐受的烯丙基阳离子才发生电环化。通常，吸电子取代基的存在使环失活并不利于环化。相反，含有给电子取代基的体系的环化选择性取决于给电子基团的性质和位置。在间位的供电子取代基特别有利于环化。如亲电子芳族取代反应所建议的，环化选择性与计算的电子密度没有明显的相关性。然而，通过气相（B3LYP / 6-31G * + ZPVE）比较环化相对速率所确定的计算选择性与观察到的选择性非常吻合。环化计算的过渡态结构与阳离子π4一致一个conrotatory electrocyclization机制。在一些涉及更多电子缺陷系统的情况下，最初形成的1 H-茚进行后续的烯烃异构化为3 H-茚。在一个实例中，发生不寻常的二聚

  DOI：

  10.1021/jo100275q
• 作为产物：
  描述：

  对硝基苯甲醛 、 苯丙酮 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以77.4%的产率得到(E)-2-methyl-3-(4-nitrophenyl)-1-phenyl-2-propen-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of α-methyl-chalcone for anti-cervical cancer activity

  摘要：

  A series of 31 chalcones were synthesized and evaluated for anti-proliferative activity against the human cervical cancer cell lines (HeLa and SiHa). Compound 19, (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino)phenyl)-2-methylprop-2-en-1-one was found to be an effective anti-proliferative agent in HeLa and SiHa cells (IC50 = 0.035 mu M). Compound 19 increased the percentage of apoptosis in a dose-dependent manner, as measured by Annexin V-FITC (fluorescein isothiocyanate)/(propidium iodide) PI staining. Molecular modeling studies of compound 19 showed that the most potent structure was docked at the yeast 20 S proteasome binding site (Protein Data Bank code-3E47) and was stabilized in the cavity by various hydrophobic and hydrogen bonding interactions.

  DOI：

  10.1007/s00044-017-1891-0

文献信息

• Barluenga's reagent with HBF₄as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes
  作者：Kosuke Murai、Keiichiro Tateishi、Akio Saito

  DOI：10.1039/c6ob02090a

  日期：——

  Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.

  用HBF 4处理的Barluenga试剂（IPy 2 BF 4，Py =吡啶）可有效催化未活化炔烃与醛或酮的分子间和分子内炔烃羰基复分解反应，其中大部分在室温下进行。这项工作代表了Barluenga试剂的首次催化应用。
• Aldolases as Leitmotiv - A Nonenzymatic Domino Aldol Reaction Triggered by Zinc Bisenolate and Polyenolate (ate) Complexes
  作者：Michael Schmittel、Manas K. Ghorai

  DOI：10.1055/s-2001-18766

  日期：——

  A new zinc(II) mediated sequential aldol reaction is described for the diastereoselective one-pot synthesis of tetrahydropyran-2,4-diols. The dependence of the yield on the ratio Zn2 +/enolate proposes that zinc(II) polyenolate and ate complexes may be involved.

  描述了一种新的锌(II)介导的顺序醛醇反应，用于非对映选择性地一次合成四氢吡喃-2,4-二醇。根据产率与 Zn2 +/烯酸盐比率的关系，推测可能涉及多烯酸盐锌（II）和ate 配合物。
• Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents:  Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄
  作者：Jong Uk Rhee、Michael J. Krische

  DOI：10.1021/ol050838x

  日期：2005.6.1

  The first use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4) and Lewis acid (BF3) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne-carbonyl metathesis.
• Toke, Laszlo; Clementis, Gyoergy; Petnehazy, Imre, Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 111, p. 183
  作者：Toke, Laszlo、Clementis, Gyoergy、Petnehazy, Imre、Jaszay, Zsuzsa M.、Toempe, Peter

  DOI：——

  日期：——
• ZIELINSKI W., POL. J. CHEM., 1980, 54, NO 11-12 2209-2215
  作者：ZIELINSKI W.

  DOI：——

  日期：——