2-ethyl-3-(thiophene-2-carbonyl)-chromen-4-one | 864433-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-ethyl-3-(thiophene-2-carbonyl)-chromen-4-one
• 英文别名: 2-Ethyl-3-(thiophene-2-carbonyl)chromen-4-one；2-ethyl-3-(thiophene-2-carbonyl)chromen-4-one
• CAS: 864433-07-8
• 化学式: C₁₆H₁₂O₃S
• 分子量: 284.335
• InChiKey: OBZQFAPKPRSVLC-UHFFFAOYSA-N

物化性质

• 沸点：
  413.7±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-(thiophene-2-carbonyl)-chromen-4-one 在 aluminum (III) chloride 、 溴 、 potassium carbonate 、 硫代乙酰胺 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 S-{2-[5-(3-methyl-9-oxo-9H-thieno[3,4-b]chromen-1-yl)thiophen-2-yl]-2-oxoethyl}ethanethioate
  参考文献：
  名称：

  Synthesis of new fluorescent 1-(thien-2-yl)-9H-thieno[3,4-b]-chroman-9-ones and their fluorescent photomodulation by photochromic dihetarylethenes

  摘要：

  New fluorescent derivatives of 1-(thien-2-yl)-3-methyl-9H-thieno[3,4-b]-chroman-9-one are synthesized and their spectral properties studied. The prepared fluorescent compounds are combined with several photochromic benzothienyl dihetarylethenes to provide mixed systems exhibiting reversible photo-induced fluorescence modulation in solution. The obtained results are promising for the development of polymeric photochromic recording media with a non-destructive fluorescence readout of optical information for RAM with extra large information capacity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.101
• 作为产物：
  描述：

  2-噻吩甲酰氯 在 吡啶 、 氢氧化钾 、 三乙胺 作用下， 以 吡啶 为溶剂， 生成 2-ethyl-3-(thiophene-2-carbonyl)-chromen-4-one
  参考文献：
  名称：

  Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

  摘要：

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.058

文献信息

• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of new fluorescent 1-(thien-2-yl)-9H-thieno[3,4-b]-chroman-9-ones and their fluorescent photomodulation by photochromic dihetarylethenes
  作者：K.S. Levchenko、V.A. Barachevski、O.I. Kobeleva、O.V. Venidiktova、T.M. Valova、A.M. Bogacheva、K.A. Chudov、E.P. Grebennikov、P.S. Shmelin、N.O. Poroshin、G.E. Adamov、V.N. Yarovenko、M.M. Krayushkin

  DOI：10.1016/j.tetlet.2015.01.101

  日期：2015.2

  New fluorescent derivatives of 1-(thien-2-yl)-3-methyl-9H-thieno[3,4-b]-chroman-9-one are synthesized and their spectral properties studied. The prepared fluorescent compounds are combined with several photochromic benzothienyl dihetarylethenes to provide mixed systems exhibiting reversible photo-induced fluorescence modulation in solution. The obtained results are promising for the development of polymeric photochromic recording media with a non-destructive fluorescence readout of optical information for RAM with extra large information capacity. (C) 2015 Elsevier Ltd. All rights reserved.