(E)-5-(4-methoxyphenyl)-1-phenylpent-2-en-4-yn-1-one | 1514900-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-(4-methoxyphenyl)-1-phenylpent-2-en-4-yn-1-one
• CAS: 1514900-12-9
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: LKBIAMSNOIYJET-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-methoxyphenyl)-1-phenylpent-2-en-4-yn-1-one 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 、 四氯化钛 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 ethyl 2-diazo-7-(4-methoxyphenyl)-3,6-dioxo-5-(2-oxo-2-phenylethyl)heptanoate
  参考文献：
  名称：

  4 H-环戊基[ c ]呋喃-5（6 H）-one衍生物的合成

  摘要：

  在Ph 3 PAuCl / AgOTf / TsOH体系中，将2-重氮-5-炔基-1,7-二酮羰基化合物转化为重氮呋喃。Rh 2（OAc）4介导的重氮呋喃衍生物向4 H -cyclopenta [ c ] furan-5（6 H）-one衍生物的转化是通过C（sp 2）-H插入反应在4位上完成的。呋喃环。

  DOI：

  10.1016/j.tet.2020.131421
• 作为产物：
  描述：

  3-(4-methoxyphenyl)propynal 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 12.0h， 以89%的产率得到(E)-5-(4-methoxyphenyl)-1-phenylpent-2-en-4-yn-1-one
  参考文献：
  名称：

  A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans

  摘要：

  A novel and efficient method for the synthesis of diversely functionalized furans is developed via DBU-mediated tandem Michael addition/5-exo-dig-cycloisomerization of enynes and keto-methylenes. This [3 + 2]-annulation is operationally simple under metal-free reaction conditions with 100% atom economy and broad substrate scope.

  DOI：

  10.1021/jo4023342

文献信息

• Applications of Thermal Activation, Ball-milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides
  作者：Żaneta A. Ignatiuk、Mikołaj J. Janicki、Robert W. Góra、Krzysztof Konieczny、Rafał Kowalczyk

  DOI：10.1002/adsc.201801498

  日期：2019.3.5

  to conjugated en‐ynones was performed through the application of chiral squaramides. Three non‐classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball‐milling. Hydrogen‐bonding catalysis was effective in all these methods, providing 1,4‐addition products in high yields and

  硝基甲烷的立体选择性加成是通过应用手性方酰胺来实现的。测试了三种促进加成反应的非经典方法，包括双相水性体系中无机碱对亲核试剂的活化，热活化和球磨。氢键催化在所有这些方法中均有效，以高收率和高达98％的立体选择性提供1,4加成产物，需要1-5 mol％的金鸡纳生物碱方酸酰胺。
• Stereoselective, Cascade Synthesis of <i>trans</i>-Enynones through Coupling-Isomerization Reaction
  作者：Bhavani Shankar Chinta、Beeraiah Baire

  DOI：10.1021/acs.joc.5b01780

  日期：2015.10.16

  A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step.
• Transformations of Conjugated Enynones in the Superacid CF₃SO₃H. Synthesis of Butadienyl Triflates, Indanones, and Indenes
  作者：Steve Saulnier、Alexander A. Golovanov、Alexandr Yu. Ivanov、Irina A. Boyarskaya、Aleksander V. Vasilyev

  DOI：10.1021/acs.joc.5b02785

  日期：2016.3.4

  Conjugated 1,5-diarylpent-2-en-4-yn-1-ones add the superacid CF3SO3H to the acetylenic bond with formation of the corresponding butadienyl triflates. Under superacidic reaction conditions, these triflates are transformed into indanone or indene derivatives depending on which substituents on the aromatic ring are conjugated with the butadiene fragment. In a less acidic system (10% vol pyridine in CF3SO3H) only the formation of butadienyl triflates takes place. Cationic reaction intermediates were studied by means of NMR and DFT calculations.