(E)-4-(p-Methoxyphenyl)-3-phenylbuten-2-one | 13938-22-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-(p-Methoxyphenyl)-3-phenylbuten-2-one
• 英文别名: (E)-4-(4-methoxyphenyl)-3-phenylbut-3-en-2-one
• CAS: 13938-22-2
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: AJFPBFJFTYMQKK-ATVHPVEESA-N

物化性质

• 熔点：
  47-49 °C
• 沸点：
  416.1±33.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-4-(p-Methoxyphenyl)-3-phenylbuten-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 3-(4-methoxyphenyl)-2-phenylacrylic acid
  参考文献：
  名称：

  A New Route to Stilbene α-Ketol Derivatives

  摘要：

  DOI：

  10.1246/bcsj.40.417
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-phenylbuta-2,3-dien-1-ol 在 iron(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(E)-4-(p-Methoxyphenyl)-3-phenylbuten-2-one
  参考文献：
  名称：

  迈伦-舒斯特型重排在烯丙醇中的酸催化合成α，β-二取代共轭烯酮

  摘要：

  考虑到铁（III）物种和质子的便宜性和环境友好性，开发了一种新颖，直接，简单的方法，可在可持续的金属催化环境下从α-烯醇中获得α，β-二取代的共轭烯酮。

  DOI：

  10.1002/adsc.201400928

文献信息

• Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H <i>O</i> -Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air
  作者：Yinsong Zhao、Shiqing Li、Xuesong Zheng、Junbin Tang、Zhijie She、Ge Gao、Jingsong You

  DOI：10.1002/anie.201612147

  日期：2017.4.3

  An unprecedented Rh‐catalyzed ketone‐directed vinylic C−H activation/[4+2] O‐annulation of α‐aryl enones with internal alkynes followed by a Cu‐catalyzed ring contraction in air to provide multiaryl‐substituted furan derivatives has been developed. The preliminary mechanism study identifies the active pyrylium salt as the key intermediate.

  已经开发出空前的Rh催化的酮基乙烯指导的CH-H活化/ α-芳基烯酮与内部炔烃的[4 + 2] O环化反应，然后在空气中进行Cu催化的环收缩以提供多芳基取代的呋喃衍生物。 。初步机理研究确定了活性吡啶盐为关键中间体。
• Regio- and Stereochemical Aspects of the Palladium-Catalyzed Desilylation−Arylation of Substituted Vinylsilanes
  作者：Davide Alvisi、Errol Blart、Bianca Flavia Bonini、Germana Mazzanti、Alfredo Ricci、Paolo Zani

  DOI：10.1021/jo960301k

  日期：1996.1.1

  The palladium-catalyzed desilylation-arylation of substituted vinylsilanes by p-iodoanisole in the presence of bidentate phosphine ligands is described. Apart from enhancing the rate of the reaction considerably, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the chelation-controlled desilylation-arylation reaction

  描述了在二齿膦配体的存在下，通过对碘苯甲醚的钯催化的取代的乙烯基硅烷的甲硅烷基化-芳基化。除了显着提高反应速率外，乙烯基硅烷部分中基于杂原子的官能团对区域化学有深远的影响。提出了涉及五元和六元螯合环的螯合可控制的硅烷化-芳基化反应的催化循环。
• Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted α,β-Unsaturated Acyclic Ketones: Enantioselective Total Synthesis of (−)-Mesembrine
  作者：Qian-Qian Zhang、Jian-Hua Xie、Xiao-Hui Yang、Jian-Bo Xie、Qi-Lin Zhou

  DOI：10.1021/ol302842h

  日期：2012.12.21

  A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (−)-mesembrine (34% yield, 12 steps).

  已经开发了由手性螺铱配合物催化的α-取代的α，β-不饱和无环酮的高效不对称氢化，用于制备手性2-取代的烯丙基醇（ee高达99.7％）。该方法提供了通往（-）-中间膜的简洁途径（34％的产率，12个步骤）。
• Synthesis and Antimicrobial Evaluation of Some Pyrazole Derivatives
  作者：Essam Mohamed Sharshira、Nagwa Mohamed Mahrous Hamada

  DOI：10.3390/molecules17054962

  日期：——

  Reaction of a series of (E)-3-phenyl-4-(p-substituted phenyl)-3-buten-2-ones with p-sulfamylphenyl hydrazine in glacial acetic acid gave the corresponding hydrazones, subsequent treatment of which with 30% HCl afforded pyrazole-1-sulphonamides. On the other hand, refluxing of chalcones with either thiosemicarbazide or isonicotinic acid hydrazide in ethanol containing a few drops of acetic acid gave pyrazoline-1-thiocarboxamides and isonicotinoyl pyrazolines, respectively. The structures of the synthesized compounds were determined on the basis of their elemental analyses and spectroscopic data. The antimicrobial activity of the newly isolated heterocyclic compounds was evaluated against Gram-positive, Gram-negative bacteria and fungi. Most of the compounds showed a moderate degree of potent antimicrobial activity.

  一系列(E)-3-苯基-4-(对取代苯基)-3-丁烯-2-酮与对磺酰胺基苯基肼在冰醋酸中反应，得到相应的肼，随后用 30% HCl 处理，得到吡唑-1-磺酰胺。另一方面，在含有几滴乙酸的乙醇中将查耳酮与硫代氨基甲酰肼或异烟酸酰肼回流，可分别得到吡唑啉-1-硫代羧酰胺和异烟酰基吡唑啉。根据元素分析和光谱数据确定了合成化合物的结构。评估了新分离的杂环化合物对革兰氏阳性菌、革兰氏阴性菌和真菌的抗菌活性。大多数化合物显示出中等程度的强效抗菌活性。
• Singlet Photochemistry of Vinyl Cyclopropenes: Regioselectivity and Mechanism; Mechanistic and Exploratory Organic Photochemistry
  作者：Howard E. Zimmerman、David W. Wilson

  DOI：10.1021/jo00108a036

  日期：1995.2

  A study of the direct photochemistry of 1-anisyl-2-phenyl-3-methyl-3-isobutenylcyclopropene (5) was pursued with the objective of elucidating the reaction regioselectivity and casting light on alternative reaction mechanisms for this reaction known to afford cyclopentadienes. Two mechanisms had previously been advanced-one proceeding by an initial three-ring bond fission to afford an intermediate vinyl carbene and the other by vinyl-vinyl bonding to afford a housane diradical intermediate. The two reaction mechanisms predict different reaction regiochemistry. The experimental observation in the case of vinylcyclopropene 5 was a preference for formation of that product in which the C1-C3 three-ring single bond is severed to give an anisyl-substituted carbene. Then bonding occurs between the isobutenyl moiety and the carbene center. CASSCF computations mere run on S-1 of the reactant cyclopropene as well as S-0 and S-1 of the two regioisomeric carbenes. The preferred carbene, both in the ground state and the first excited singlet, was that having the anisyl group on the carbene center. The S-1 carbenes were Linear at the carbene center while the S-0 carbenes were bent. The aryl group at the carbene center of S-1 preferred to overlap with a pentadienyl pi-system. The lower energy of the excited singlet carbenes with anisyl at the carbene center accounts for the regioselectivity of opening with internal conversion occurring during or subsequent to bond stretching.