(E)-1-(4-chlorophenyl)-5-phenylpent-1-en-4-yn-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(4-chlorophenyl)-5-phenylpent-1-en-4-yn-3-one
• 化学式: C₁₇H₁₁ClO
• 分子量: 266.727
• InChiKey: REYJGSVHUYNKTA-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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-1-en-4-yn-3-one 在 硫酸 、 水 作用下， 以 氯仿 为溶剂， 反应 96.0h， 以89%的产率得到2-(4-chlorophenyl)-2,3-dihydro-6-phenylpyran-4-one
  参考文献：
  名称：

  布朗斯台德酸促进交叉共轭烯酮环化成二氢吡喃-4-酮

  摘要：

  在三氟甲磺酸或硫酸中，二芳基取代的交叉共轭烯炔酮将酸加成到碳-碳三键上，得到相应的乙烯基三氟甲磺酸酯或硫酸酯。乙烯基三氟甲磺酸酯在水性后处理下是稳定的，而乙烯基硫酸酯水解为 α,β-不饱和 1,3-二酮（以共轭烯醇形式存在）。延长的反应时间导致环化成二氢吡喃-4-酮，产率高达 95%。分别在三氟甲磺酸和硫酸中质子化形式的乙烯基三氟甲磺酸酯或硫酸盐作为反应中间体通过 NMR 光谱进行研究。讨论了形成二氢吡喃-4-酮的合理反应机制。

  DOI：

  10.1002/ejoc.201700423
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-1-(4-chlorophenyl)-5-phenylpent-1-en-4-yn-3-one
  参考文献：
  名称：

  硫叶立德酸介导的多米诺苯环化战略，以构建联芳基，烯化和炔化的苯衍生物

  摘要：

  AbstractAn efficient domino benzannulation strategy with the participation of sulfur ylides for the construction of biaryl compounds is disclosed. It could also be extended to the synthesis of alkenylated and alkynylated benzene derivatives under mild conditions. This versatile strategy combined with traditional metal‐catalyzed cross‐coupling methods should offer a practical route to construct complex multiaryl compounds.magnified image

  DOI：

  10.1002/adsc.201400176

文献信息

• TfOH-Promoted Reactions of TMS-Ethers of CF₃–Pentenynoles with Arenes. Synthesis of CF₃-Substituted Pentenynes, Indenes, and Other Carbocyclic Structures
  作者：Aleksey V. Zerov、Irina A. Boyarskaya、Olesya V. Khoroshilova、Irina N. Lavrentieva、Alexander V. Slita、Ekaterina O. Sinegubova、Vladimir V. Zarubaev、Aleksander V. Vasilyev

  DOI：10.1021/acs.joc.0c02361

  日期：2021.1.15

  react with arenes in the presence of 1.5 equiv of TfOH forming regio- and stereoselectively E-1,1,5-triaryl-3-(trifluoromethyl)-pent-2-en-4-ynes [Ar–C≡C–C(CF3)═CH–CHAr′(Ar″)] in good yields. In the excess of TfOH, these CF3-pentenynes are further intramolecularly cyclized into CF3-bicyclic dihydroanthracene derivatives (“helicopter”-like molecules). The CF3-pentenynes may also react with arenes, as external

  1,5-二芳基-3-（三氟甲基）-pent-1-en-4-yn-3-oles [Ar–C≡C–C（CF 3）（OSiMe 3）–CH═CH–Ar的三甲基甲硅烷基醚']在超强酸TfOH中产生反应性共轭CF 3-烯丙基-炔丙基阳离子[Ar–C≡CC–C +（CF 3）–CH═CH–Ar']。这些物质在1.5当量的TfOH存在下与芳烃反应，形成区域选择性和立体选择性的E- 1,1,5-三芳基-3-（三氟甲基）-戊-2-烯-4-炔[Ar–C≡C– C（CF 3）═CH–CHAr'（Ar''）]，收率高。在过量的TfOH中，这些CF 3-戊烯炔进一步分子内环化为CF 3-双环二氢蒽衍生物（“直升机”样分子）。CF 3-戊烯也可以作为外部亲核试剂与芳烃反应，生成CF 3-茚。这两个主要反应途径取决于CF 3-戊烯炔中芳基取代基的内部亲核性和芳族分子的外部亲核性。已经讨论了合理的阳离子反应机理。已经研究了CF
• A General Synthesis of Cross-Conjugated Enynones through Pd Catalyzed Sonogashira Coupling with Triazine Esters
  作者：Dezhi Lin、Yunfang Liu、Hongyu Yang、Xiao Zhang、Huaming Sun、Yajun Jian、Weiqiang Zhang、Jianming Yang、Ziwei Gao

  DOI：10.3390/molecules28114364

  日期：——

  susceptibility of the unsaturated C-C bonds adjacent to the carbonyl group toward Pd catalysts makes the direct conversion of α, β-unsaturated derivatives as acyl electrophiles to cross-conjugated ketones rare. This work presents a highly selective C-O activation approach to prepare cross-conjugated enynones using α, β-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free

  钯催化的 α, β-不饱和酸衍生物的 Sonogashira 偶联为交叉共轭烯酮提供了一种面向多样性的合成策略。然而，与羰基相邻的不饱和CC键对Pd催化剂的敏感性使得α，β-不饱和衍生物作为酰基亲电子试剂直接转化为交叉共轭酮很少见。这项工作提出了一种高选择性的 CO 活化方法，使用 α, β-不饱和三嗪酯作为酰基亲电子试剂制备交叉共轭烯酮。在无碱和膦配体的条件下，NHC-Pd(II)-烯丙基预催化剂单独有效催化 α, β-不饱和三嗪酯与末端炔烃的交叉偶联，产生 31 个具有不同官能团的交叉共轭烯酮。
• Rele, Dinesh N.; Baskaran; Korde, Shilpa S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 431 - 436
  作者：Rele, Dinesh N.、Baskaran、Korde, Shilpa S.、Vora, Jyoti D.、Trivedi, Girish K.

  DOI：——

  日期：——
• Azolyl-substituted 1,2,3-triazoles
  作者：A. A. Golovanov、I. S. Odin、V. V. Bekin、A. V. Vologzhanina、I. S. Bushmarinov、S. S. Zlotskii、Yu. L. Gerasimov、P. P. Purygin

  DOI：10.1134/s1070428016030209

  日期：2016.3

  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.
• Synthesis of New N-Acyl-1,2,3-triazole Chalcones and Determination of Their Antibacterial Activity
  作者：I. S. Odin、S. Cao、D. Hughes、E. V. Zamaratskii、Yu. P. Zarubin、P. P. Purygin、A. A. Golovanov、S. S. Zlotskii

  DOI：10.1134/s0012500820360021

  日期：2020.6

  Previously unknown N-acyl derivatives of 1,2,3-triazole chalcones have been prepared by the acylation of the potassium salts of 4-(3-oxo-3-phenylprop-1-en-1-yl)-5-phenyl-1,2,3-triazolides with carboxylic acid chlorides. The introduction of theN-acyl residue into the heterocyclic moiety of 1-aryl-3-(1H-1,2,3-triazol-4-yl)prop-2-en-1-ones has been shown to afford compounds with antibacterial activity.