(1E,4E)-1-phenyl-5-(thiophen-2-yl)penta-1,4-dien-3-one | 1023-68-3

• 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: (1E,4E)-1-phenyl-5-(thiophen-2-yl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-phenyl-5-(2-thienyl)penta-1,4-dien-3-one；(E,E)-1-Phenyl-5-(2-thienyl)-1,4-pentadien-3-one；E,E-1-(2-thienyl)-5-phenyl-1,4-pentadien-3-one；(1E,4E)-1-phenyl-5-thiophen-2-ylpenta-1,4-dien-3-one
• CAS: 1023-68-3
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: QFVDNWDUBVJAHH-BNFZFUHLSA-N

物化性质

• 沸点：
  409.5±38.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-phenyl-5-(thiophen-2-yl)penta-1,4-dien-3-one 在 dipotassium hydrogenphosphate 、 sodium hydrogensulfide 作用下， 以 水 、 异丙醇 为溶剂， 以86%的产率得到2,3,5,6-Tetrahydro-2-phenyl-6-(2-thienyl)thiopyran-4-one
  参考文献：
  名称：

  Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane

  摘要：

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.

  DOI：

  10.1021/jo00111a027
• 作为产物：
  描述：

  2,3,5,6-Tetrahydro-2-phenyl-6-(2-thienyl)thiopyran-4-one 在 过氧乙酸 、 硫酸 、 碘 、 二甲基亚砜 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (1E,4E)-1-phenyl-5-(thiophen-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane

  摘要：

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.

  DOI：

  10.1021/jo00111a027

文献信息

• A Broad‐Spectrum Synthesis of Tetravinylethylenes
  作者：Kelsey L. Horvath、Christopher G. Newton、Kimberley A. Roper、Jas S. Ward、Michael S. Sherburn

  DOI：10.1002/chem.201900550

  日期：2019.3.15

  compounds of the tetravinylethylene (TVE) family is reported. Ramirez‐type dibromo‐olefination of readily accessible penta‐1,4‐dien‐3‐ones generates 3,3‐dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki–Miyaura or Mizoroki–Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically substituted tetravinylethylenes with up to three

  报道了四乙烯基乙烯（TVE）家族化合物的第一个一般合成。容易获得的五-1,4-二烯-3-酮的拉米雷斯型二溴烯烃化反应生成3,3-二溴[3]树枝状烯，它们经历了两次Negishi，Suzuki-Miyaura或Mizoroki-Heck反应，并带有多种烯烃耦合伙伴。该途径提供了范围广泛的不对称取代的四乙烯基乙烯，其具有多达三个不同的烯基取代基连接至中央C = C键。该方法的广泛范围通过制备第一个更高阶的通过共轭/交叉共轭杂化化合物形成的低级烯烃。显示不对称取代的TVE经历了具有高位点选择性和非对映选择性的多米诺骨化电环化反应，
• Quinine-Catalysed Double Michael Addition of Malononitrile to 1,5-Disubstituted Pentadien-3-ones: A Stereoselective Route to Cyclohexanones
  作者：Claudia De Fusco、Alessandra Lattanzi

  DOI：10.1002/ejoc.201100282

  日期：2011.7

  The stereoselective synthesis of 4-oxo-2,6-diaryl-cyclohexane-1,1-dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5-disubstituted pentadien-3-ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate-to-good yields, excellent diastereoselectivity and up to 86 % ee. The isolation of the monoaddition product helps to shed light

  4-氧代-2,6-二芳基-环己烷-1,1-二腈的立体选择性合成是通过丙二腈与奎宁催化的1,5-二取代戊二烯-3-酮的双迈克尔加成而开发的。这种简单的级联过程以中等至良好的产率、出色的非对映选择性和高达 86% 的 ee 提供了环己酮。单加成产物的分离有助于阐明两步法的立体化学结果。
• Aromatic heterocyclic-substituted cyclic sulfone compounds and
  申请人：Eastman Kodak Company

  公开号：US05352802A1

  公开（公告）日：1994-10-04

  Certain chemical compounds, which are aromatic heterocyclic-substituted derivatives of 4H-thiopyran-1,1-dioxide, are electron-transport agents. These compounds exhibit good speed and toe voltage properties in electrophotographic elements.

  某些化学化合物，它们是4H-硫杂环戊二烯-1,1-二氧化物的芳香族杂环取代衍生物，是电子传输剂。这些化合物在电子照相元件中表现出良好的速度和趾电压特性。
• A Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives
  作者：Vijay Nair、Smitha C. Mathew、Akkattu T. Biju、Eringathodi Suresh

  DOI：10.1002/anie.200604025

  日期：2007.3.12
• Heteroaromatic Analogues of Dibenzylideneacetone (dba) and Pd⁰₂(het-dba)₃ Complexes: Effect of a Thienyl Moiety on the Reactivity of Pd⁰(η²-th_<i>n</i>-dba)(PPh₃)₂/Pd⁰(PPh₃)₂ (<i>n</i> = 1 or 2) and Pd⁰(η²-th₂-dba)(dppe)/Pd⁰(dppe) in Oxidative Addition Reactions with Iodobenzene
  作者：Petr Sehnal、Hanaa Taghzouti、Ian J. S. Fairlamb、Anny Jutand、Adam F. Lee、Adrian C. Whitwood

  DOI：10.1021/om800975w

  日期：2009.2.9

  Palladium(0) complexes containing thienyl analogues of dibenzylidene acetone (dba) have been synthesized and characterized. Their reactivity toward PPh3 and dppe, to generate Pd-0(eta(2)-alkene)(PPh3)2 and Pd-0(eta(2)-alkene)(dppe) complexes, and their subsequent oxidative addition reactions with PhI, have been investigated.