(E)-1-(furan-2-yl)-5-phenylpent-2-en-4-yn-1-one | 1257555-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(furan-2-yl)-5-phenylpent-2-en-4-yn-1-one
• 英文别名: 1-(2-furyl)-5-phenylpent-2-en-4-yn-1-one
• CAS: 1257555-48-8
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: RRLBBTRBPIITCQ-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(furan-2-yl)-5-phenylpent-2-en-4-yn-1-one 、 苄硫醇 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以81%的产率得到3-benzylsulfanyl-1-(furan-2-yl)-5-phenylpent-4-yn-1-one
  参考文献：
  名称：

  Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones

  摘要：

  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.

  DOI：

  10.1134/s1070428014010035
• 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-(furan-2-yl)-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

• 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。
• 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.
• 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.