(E,E)-1,5-Di(3-thienyl)-1,4-pentadien-3-one | 156147-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E,E)-1,5-Di(3-thienyl)-1,4-pentadien-3-one
• 英文别名: E,E-1,5-di-(3-thienyl)-1,4-pentadien-3-one；(1E,4E)-1,5-di(thiophen-3-yl)penta-1,4-dien-3-one
• CAS: 156147-12-5
• 化学式: C₁₃H₁₀OS₂
• 分子量: 246.354
• InChiKey: GYLLWOUNQDFIEU-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,E)-1,5-Di(3-thienyl)-1,4-pentadien-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-2,6-di(3-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-2,6-di(3-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 (E,E)-1,5-Di(3-thienyl)-1,4-pentadien-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

• 13C and 1H NMR of 2,6-diaryl-1-hydroxy piperidin-4-one oximes; substituent effects on cis/trans ratio and conformational equilibria
  作者：E. Dı́az、H. Barrios、F. del Rı́o Portilla、A. Guzmán、J.L. Aguilera、R. Becerril、C.K. Jankowski、W.F. Reynolds

  DOI：10.1016/s1386-1425(00)00282-1

  日期：2000.10

  The reaction of substituted diarylidene acetones with hydroxylamine hydrochloride affords isomeric N-hydroxy diaryl piperidinone oximes as main products. The structures as well as conformational equilibria of these products were established by 1H and 13C NMR spectroscopy and further studied by variable temperature NMR. It was found that the cis/trans ratio of 2,6-substituted piperidine derivatives

  取代的二亚芳基丙酮与盐酸羟胺的反应得到异构体的N-羟基二芳基哌啶酮肟为主要产物。通过1H和13C NMR光谱确定了这些产物的结构和构象平衡，并通过变温NMR进行了进一步研究。发现2，6-取代的哌啶衍生物的顺/反比取决于芳环上取代基的位置。
• Cyclodimerization of α,β-α′,β′-unsaturated ketones promoted by samarium diiodide. Complete assignment of the¹H and¹³C NMR spectra of hydroxycyclopentylpropenone derivatives
  作者：Ronan Le Lagadec、María Isabel Chávez、Laura Rubio、Armando Cabrera

  DOI：10.1002/mrc.823

  日期：2001.4

  The 1H and 13C NMR chemical shift assignments of hydroxycyclopentylpropenone derivatives, prepared by a highly selective reaction between samarium(II) iodide and unsaturated ketones, are described. Two‐dimensional shift‐correlated experiments (COSY, HMBC, HMQC, NOESY) were used to assign the chemical shifts completely and unambiguously. Copyright © 2001 John Wiley & Sons, Ltd.

  描述了由碘化钐 (II) 和不饱和酮之间的高选择性反应制备的羟基环戊基丙烯酮衍生物的 1 H 和 13 C NMR 化学位移分配。二维位移相关实验（COSY、HMBC、HMQC、NOESY）用于完全明确地分配化学位移。版权所有 © 2001 John Wiley & Sons, Ltd.
• Aromatic heterocyclic-substituted cyclic sulfone compounds and
  申请人：Eastman Kodak Company

  公开号：US05300385A1

  公开（公告）日：1994-04-05

  Certain chemical compounds, which are aromatic heterocyclic-substituted derivatives of 4H-thiopyran-1,1,-dioxide given by the formula (I) wherein Het is a substituted or unsubstituted heterocyclic ring system containing at least one 5-membered heterocyclic aromatic ring; and R is an alkyl, aralkyl, or cycloalkyl group of 1 to about 10 carbon atoms, or an aryl group of 6 to about 12 carbon atoms, or a substituted or unsubstituted heterocyclic ring system containing at least one 5-membered aromatic heterocyclic ring, are electron-transport agents. These compounds exhibit good speed and toe voltage properties in electrophotographic elements. ##STR1##

  某些化学化合物是4H-硫代吡喃-1,1-二氧化物的芳香族杂环取代衍生物，其化学式为（I），其中Het是含有至少一个5-成员芳香族环的取代或未取代的杂环环系；R是1到约10个碳原子的烷基，芳基烷基或环烷基，或6到约12个碳原子的芳基，或含有至少一个5-成员芳香族杂环的取代或未取代的杂环环系，这些化合物是电子传输剂。这些化合物在电子照相元件中表现出良好的速度和灵敏度特性。##STR1##
• Shining Light on the Solution- and Excited-State Dynamics of Chalcogenopyrylium Polymethine Dyes
  作者：Lauren E. Rosch、Matthew R. Crawley、Ryan M. O’Donnell、Thomas N. Rohrabaugh、Trenton R. Ensley、Thomas A. Sobiech、Timothy R. Cook

  DOI：10.1021/acs.organomet.2c00263

  日期：2022.8.22

  singlet oxygen yields as high as 12% for certain dyes, we observe no evidence for 1O2 from direct phosphorescence measurements. We now fill in many of these gaps through steady-state and pulsed-laser kinetic experiments on a family of 14 dyes, including six novel dyes, selected to vary physical and electronic structure. These structural changes encompass the selenium and tellurium heteroatoms, phenyl,

  尽管 40 年来人们对硫属吡喃多甲炔染料感兴趣，但我们对其光物理特性的理解仍存在重大差距。这些差距阻碍了将这些染料应用为光动力疗法和/或生物医学传感剂的努力，其中完全了解它们的激发态动力学和化学是很重要的。例如，尽管先前的报道确定某些染料的单线态氧产量高达 12%，但我们没有观察到1 O 2的证据来自直接磷光测量。我们现在通过对 14 种染料家族（包括六种新型染料）进行稳态和脉冲激光动力学实验来填补这些空白，这些染料被选为改变物理和电子结构。这些结构变化包括硒和碲杂原子、苯基、噻吩、叔-丁基取代基和次甲基接头长度。通过飞秒瞬态吸收光谱获得激发态寿命。寿命都低于 300 ps，这表明它们的激发态会快速弛豫。值得注意的是，我们没有观察到任何三重态瞬态过程的证据。磷光仅在 77 K 的样品中观察到。变温 NMR 实验表明，吡喃环围绕次甲基骨架的旋转是这些染料动力学的关键决定因素，从而将它们的光物
• US5300385A
  申请人：——

  公开号：US5300385A

  公开（公告）日：1994-04-05