(E)-1-(4-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-one | 1257555-45-5

• 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-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-one
• 英文别名: 1-(4-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-one
• CAS: 1257555-45-5
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: GXNPHWISWLMAMT-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-one 在 叠氮化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-1-(4-methoxyphenyl)-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one
  参考文献：
  名称：

  Azolyl-substituted 1,2,3-triazoles

  摘要：

  Huisgen reaction of (E)-1,5-diarylpent-2-en-4-yn-1-ones and (E)-1,5-diarylpent-1-en-4-yn-3-ones afforded 1-aryl-3-(5-aryl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones and 3-aryl-1-(5-aryl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, respectively. (E)-1-Aryl-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones reacted with hydrazine hydrate and phenylhydrazine to give 72-93% of 4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles which underwent dehydrogenation on heating in boiling acetic acid with formation of the corresponding pyrazole derivatives. The molecular structures of (E)-3-phenyl-1-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one and 4-[3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-5-phenyl-1H-1,2,3-triazole were studied by X-ray analysis. 4-(3-Aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles showed toxicity against Daphnia magna.

  DOI：

  10.1134/s1070428016030209
• 作为产物：
  描述：

  1'-羟基-2',3'-去氢草蒿脑 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (E)-1-(4-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-one
  参考文献：
  名称：

  Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction

  摘要：

  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.

  DOI：

  10.1021/acs.joc.5b01780

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 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。
• 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。
• Synthesis of 1,5-disubstituted (E)-pent-2-en-4-yn-1-ones
  作者：A. A. Golovanov、D. R. Latypova、V. V. Bekin、V. S. Pisareva、A. V. Vologzhanina、V. A. Dokichev

  DOI：10.1134/s1070428013090030

  日期：2013.9

  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.
• Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones
  作者：A. A. Golovanov、D. M. Gusev、A. V. Vologzhanina、V. V. Bekin、V. S. Pisareva

  DOI：10.1134/s1070428014010035

  日期：2014.1

  Regioselectivity of nucleophilic addition of benzenethiols and phenylmethanethiol to 1,5-diarylpent-2-en-4-yn-1-ones in ethanol in the presence of triethylamine at 0-30A degrees C is determined by the nucleophile nature. Phenylmethanethiol adds to the double bond, whereas benzenethiols add to the triple bond. The addition products, 1,5-diaryl-3-benzylsulfanylpent-4-yn-1-ones and 1,5-diaryl-5-(4-arylsulfanyl)penta-2,4-dien-1-ones, respectively, were isolated in 43-89% yield. Substituents in the aryl rings of the substrates did not affect the reaction direction.