3-(4-methoxylstyryl)furan | 128587-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxylstyryl)furan
• 英文别名: 3-(p-methoxystyryl)furan；3-(4-methoxystyryl)furan；3-[2-(4-Methoxyphenyl)ethenyl]furan；3-[2-(4-methoxyphenyl)ethenyl]furan
• CAS: 128587-72-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KJEYIJKGWPDCNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methoxylstyryl)furan 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 苯 为溶剂， 反应 6.0h， 以41%的产率得到2-甲氧基-7-甲基萘
  参考文献：
  名称：

  Base-induced photorearrangements from 3-styrylfurans to 2-methylnaphthalenes

  摘要：

  Irradiation of 3-(4-substituted styryl)furans in basic media yielded a series of 7-substituted-2-methylnaphthalenes, including methoxy, isopropyl, ethyl, methyl, fluoro, and cyano substituents. This base-induced photorearrangement involves cis-trans photoisomerization, 6e photocyclization, base-induced elimination, and a Norrish Type I photoreaction and is a novel method to synthesize unsymmetrical 2,7-disubstituted naphthalenes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.141
• 作为产物：
  描述：

  3-糠醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 三苯基膦 、 18-冠醚-6 、 potassium carbonate 作用下， 以 苯 、 二氯甲烷 、 水 为溶剂， 以60%的产率得到3-(4-methoxylstyryl)furan
  参考文献：
  名称：

  Base-induced photorearrangements from 3-styrylfurans to 2-methylnaphthalenes

  摘要：

  Irradiation of 3-(4-substituted styryl)furans in basic media yielded a series of 7-substituted-2-methylnaphthalenes, including methoxy, isopropyl, ethyl, methyl, fluoro, and cyano substituents. This base-induced photorearrangement involves cis-trans photoisomerization, 6e photocyclization, base-induced elimination, and a Norrish Type I photoreaction and is a novel method to synthesize unsymmetrical 2,7-disubstituted naphthalenes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.141

文献信息

• Synthesis, spectroscopic characterization and photophysics of new functionalized 2,3-distyrylfurans: Substituent and solvent effects on their photobehavior
  作者：Irena Škorić、Ilijana Kikaš、Margit Kovács、Marija Šindler-Kulyk、Ottó Horváth

  DOI：10.1016/j.jphotochem.2010.02.013

  日期：2010.4

  Two new groups of p-chloro-, p-methoxy- and p-nitro-substituted derivatives of the trans,trans-isomers of 2.3-distyrylfuran have been synthesized by a sequence of reactions according to known methods. These new conjugated heterocyclic compounds along with the parent one and its methyl-derivative have been characterized spectrally, photophysically and photochemically. These compounds, except for the nitro-derivatives, display high fluorescence quantum yields in the non-polar n-hexane (Phi(F) = 0.76-0.98). In ethanol of high polarity, the lifetime of their singlet excited state increases from 1.31-2.59 ns to 2.01-4.77 ns, significantly enhancing the quantum yield of their photochemical reaction from 0.02-0.24 to 0.25-0.46, and diminishing their fluorescence efficiency (Phi(F) = 0.26-0.64). Deviating from the other compounds studied, the quantum yields for both the fluorescence and the photolysis of the nitro-derivatives are rather low (Phi(F) < 10(-4), Phi = 0.025-0.042 in ethanol), probably due to an efficient intersystem crossing leading to a non-reactive triplet state. Accordingly, their singlet-state lifetime is also relatively short (tau(F) < 0.3 ns). (C) 2010 Elsevier B.V. All rights reserved.
• Base-induced photorearrangements from 3-styrylfurans to 2-methylnaphthalenes
  作者：Jinn-Hsuan Ho、Tunng-Hsien Lee、Chia-Kai Lo、Chao-Li Chuang

  DOI：10.1016/j.tetlet.2011.10.141

  日期：2011.12

  Irradiation of 3-(4-substituted styryl)furans in basic media yielded a series of 7-substituted-2-methylnaphthalenes, including methoxy, isopropyl, ethyl, methyl, fluoro, and cyano substituents. This base-induced photorearrangement involves cis-trans photoisomerization, 6e photocyclization, base-induced elimination, and a Norrish Type I photoreaction and is a novel method to synthesize unsymmetrical 2,7-disubstituted naphthalenes. (C) 2011 Elsevier Ltd. All rights reserved.