(E)-1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one | 943241-87-0

• 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)-1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one
• 英文别名: 1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one
• CAS: 943241-87-0
• 化学式: C₁₇H₁₁ClO
• 分子量: 266.727
• InChiKey: DQXGKKXCCYJNRI-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 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：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one 在 吡啶 、 三氟甲磺酸 作用下， 反应 5.0h， 以57%的产率得到3-(2-(4-chlorophenyl)-2-oxoethyl)indan-1-one
  参考文献：
  名称：

  Transformations of Conjugated Enynones in the Superacid CF₃SO₃H. Synthesis of Butadienyl Triflates, Indanones, and Indenes

  摘要：

  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.

  DOI：

  10.1021/acs.joc.5b02785
• 作为产物：
  描述：

  苯丙炔醛缩二乙醛 在 硫酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (E)-1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one
  参考文献：
  名称：

  Synthesis of 1,5-disubstituted (E)-pent-2-en-4-yn-1-ones

  摘要：

  The condensation of 3-arylpropynals with aryl methyl ketones in the presence of sodium hydroxide in 50% aqueous ethanol at 0A degrees C (Claisen-Schmidt reaction) afforded up to 89% of the corresponding (E)-1,5-diarylpent-2-en-4-yn-1-ones. The E configuration of the double C=C bond and cis conformation of the enone fragment in the products in crystal and CDCl3 solution were determined by X-ray analysis and H-1 NMR spectroscopy.

  DOI：

  10.1134/s1070428013090030

文献信息

• Synthesis and Cytotoxicity of Selenium-Containing Dienones
  作者：D. M. Gusev、A. S. Bunev、A. A. Golovanov

  DOI：10.1134/s1070363220020085

  日期：2020.2

  occurs regioselectively at the β-carbon of the triple bond of 1,5-disubstituted pent-2-ene-4-yne-1-ones, pent-4-ene-2-yne-1-ones and pent-1-ene-4-yne-3-ones. The resulting selenium-containing conjugated dienones exhibit pronounced cytotoxicity against some tumor cell lines.

  摘要苯并硒醇的亲核加成在1，5-二取代的戊-2-烯-4-炔-1-酮，戊-4-烯-2-炔-1-酮和pent-1-ene-4-yne-3-ones。所得的含硒共轭二烯酮对某些肿瘤细胞系表现出明显的细胞毒性。
• 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 synthesis of enynones via base-catalyzed isomerization of 1,5-disubstituted-2,4-pentadiynyl silyl ethers or their alcohol derivatives
  作者：Jingjin Chen、Guoqin Fan、Yuanhong Liu

  DOI：10.1039/c0ob00344a

  日期：——

  1,5-Disubstituted-2,4-pentadiynyl silyl ethers undergo smooth desilylative isomerization to afford cis-enynones as major products with moderate stereoselectivities in the presence of a catalytic amount of KOtBu or DBU. While the isomerization reactions of their alcohol derivatives catalyzed by KOH, KOtBu or NaH take place efficiently to produce trans-enynones with high stereoselectivities. These reactions

  1,5-二取代的2,4-戊二炔基甲硅烷基醚经过顺式脱甲硅烷基化异构化反应，以顺式-乙炔酮为主要产物，并在催化量的二甲基甲酰胺存在下，具有中等的立体选择性。KO Ť卜 或者 DBU。而其醇衍生物的异构化反应是通过酸值， KO Ť卜 或者 碳酸氢钠有效地产生具有高立体选择性的反式-乙炔酮。这些反应为合成具有广泛取代基的烯酮提供了方便实用的途径。
• Synthesis of 4H-cyclopenta[c]furan-5(6H)-one derivatives
  作者：Xianxia Tu、Haiyun Peng、Guisheng Deng

  DOI：10.1016/j.tet.2020.131421

  日期：2020.8

  Ph3PAuCl/AgOTf/TsOH system, 2-diazo-5-alkynyl-1,7-diketo carbonyl compounds were transformed into diazo furans. Rh2(OAc)4-mediated conversion of the diazo furan derivatives into 4H-cyclopenta[c]furan-5(6H)-one derivatives was accomplished via C(sp2)−H insertion reaction at 4-position on the furan ring.

  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。
• Nucleophilic addition of heterocyclic amines to conjugated enyne ketones
  作者：A. A. Golovanov、V. V. Bekin、I. S. Odin、A. Yu. Chertov、O. B. Grigor’eva、V. S. Pisareva

  DOI：10.1134/s1070428015120039

  日期：2015.12

  Nucleophilic addition of secondary heterocyclic amines (morpholine, piperidine, and piperazine) to the double or triple bond of (E)-1,5-diarylpent-2-en-4-yn-1-ones is controlled by the kinetic and thermodynamic factor, respectively. The regioselectivity of the addition of piperazine to these enynones is determined by the substituent nature in the benzene rings. Conjugated ketones with electron-donating

  仲杂环胺（吗啉，哌啶和哌嗪）的亲核加成反应是由（E）-1,5-二芳基戊-2-en-4-yn-1-one的双键或三键控制的， 分别。向这些烯酮添加哌嗪的区域选择性由苯环中的取代基性质决定。具有给电子取代基的共轭酮在双键处占据哌嗪分子，在三键处具有吸电子基团。