cis-3-(p-methoxystyryl)furan

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: cis-3-(p-methoxystyryl)furan
• 英文别名: 3-[(Z)-2-(4-methoxyphenyl)ethenyl]furan
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KJEYIJKGWPDCNJ-IHWYPQMZSA-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：

  三甲基氯硅烷 、 cis-3-(p-methoxystyryl)furan 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 、 {3-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-furan-2-yl}-trimethyl-silane
  参考文献：
  名称：

  3-芳基和3-苯乙烯基呋喃的区域选择性邻位锂化。

  摘要：

  [结构：见文字]。已经发现了3-芳基和3-苯乙烯基呋喃的邻位锂化的不寻常的区域选择性模式，其中锂化优先发生在空间受限的2-位。该结果至少部分归因于通过从在3位上附加到锂阳离子上的取代基的π-电子密度的空位给予而使中间呋喃阴离子稳定。该邻位锂化反应可以用作获得2，3-二取代的呋喃的有用的合成工具。

  DOI：

  10.1021/ol051205l
• 作为产物：
  描述：

  3-糠醛 、 4-甲氧基苄基三苯基膦溴化盐 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 trans-3-(4-methoxystyryl)furan 、 cis-3-(p-methoxystyryl)furan
  参考文献：
  名称：

  3-芳基和3-苯乙烯基呋喃的区域选择性邻位锂化。

  摘要：

  [结构：见文字]。已经发现了3-芳基和3-苯乙烯基呋喃的邻位锂化的不寻常的区域选择性模式，其中锂化优先发生在空间受限的2-位。该结果至少部分归因于通过从在3位上附加到锂阳离子上的取代基的π-电子密度的空位给予而使中间呋喃阴离子稳定。该邻位锂化反应可以用作获得2，3-二取代的呋喃的有用的合成工具。

  DOI：

  10.1021/ol051205l

文献信息

• Styrylheterocycles: A novel class of inhibitors on lipopolysaccharide-Induced nitric oxide production
  作者：Sang Kook Lee、Hye Young Min、Sun Kyung Huh、Eun-Young Kim、Eunjung Lee、Soyoung Song、Sanghee Kim

  DOI：10.1016/j.bmcl.2003.08.013

  日期：2003.11

  A series of styrylheterocycles was prepared and their inhibitory activities against nitric oxide (NO) production were evaluated in a cell culture system using lipopolysaccharide-stimulated RAW264.7 macrophage cells. Our studies have identified a new series of inhibitors on NO production, providing the basis for further development of potent inhibitors. The preliminary structure-activity relationship, to elucidate the essential structural requirements, has been described. Mechanistic studies suggest that the suppression of iNOS mRNA transcription is, at least in part, related to the inhibitory activity of styrylheterocycles. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.
• Regioselective Ortho Lithiation of 3-Aryl and 3-Styryl Furans
  作者：Maria Tofi、Thomas Georgiou、Tamsyn Montagnon、Georgios Vassilikogiannakis

  DOI：10.1021/ol051205l

  日期：2005.7.1

  for the ortho lithiation of 3-aryl and 3-styryl furans has been uncovered wherein lithiation occurs preferentially at the sterically encumbered 2-position. The results are attributed, at least in part, to stabilization of the intermediate furyl anion by through-space donation of pi-electron density from the substituent appended at the 3-position to the lithium cation. This ortho lithiation reaction

  [结构：见文字]。已经发现了3-芳基和3-苯乙烯基呋喃的邻位锂化的不寻常的区域选择性模式，其中锂化优先发生在空间受限的2-位。该结果至少部分归因于通过从在3位上附加到锂阳离子上的取代基的π-电子密度的空位给予而使中间呋喃阴离子稳定。该邻位锂化反应可以用作获得2，3-二取代的呋喃的有用的合成工具。