3-styrylfuran | 128587-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-styrylfuran
• 英文别名: 3-(2-Phenylethenyl)furan
• CAS: 128587-62-2
• 化学式: C₁₂H₁₀O
• 分子量: 170.211
• InChiKey: FGPODXIBURBNDF-UHFFFAOYSA-N

物化性质

• 沸点：
  261.4±15.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-styrylfuran 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42%的产率得到2-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 、 diphenyl benzylphosphonate 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-styrylfuran
  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

• 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。
• Nanocrystalline magnesium oxide-stabilized palladium(0): the Heck reaction of heteroaryl bromides in the absence of additional ligands and base
  作者：Mannepalli Lakshmi Kantam、Police Vishnuvardhan Redddy、Pottabathula Srinivas、Akula Venugopal、Suresh Bhargava、Yuta Nishina

  DOI：10.1039/c3cy00404j

  日期：——

  An efficient and user-friendly protocol has been realized for the Heck reaction of heteroaryl bromides by using a reusable nanocrystalline magnesium oxide-stabilized palladium(0) catalyst without the aid of additional ligands and base. Dimethylamine generated under in situ conditions by the decomposition of DMF serves as the base in this reaction. The catalyst was reused with consistent activity up

  通过使用可重复使用的纳米晶态氧化镁稳定的钯（0）催化剂，无需其他配体和碱，即可实现杂芳基溴的Heck反应的有效且用户友好的协议。 二甲胺DMF分解在原位条件下生成的油在该反应中用作碱。催化剂具有稳定的活性，可重复使用多达四个循环。
• Fungicidal thienyl propenoates
  申请人：Imperial Chemical Industries PLC

  公开号：US05073184A1

  公开（公告）日：1991-12-17

  Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteraryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8, --COR.sup.9 --CR.dbd.NR.sup.10, --CR.dbd.NOR.sup.10 or --N.dbd.CR.sup.11 R.sup.12 groups; or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12, which are the same or different, are hydrogen atoms (provided that R.sup.4 and R.sup.5 are not hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heterarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal compelxes thereof. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

  式(I)的化合物及其立体异构体，其中W为 R1O2C-C=CH-ZR2，其中R1和R2相同或不同，为烷基或氟烷基，Z为氧原子或硫原子；A为氧原子或硫原子，-NR3-或-CR4R5-；X、Y和Z1相同或不同，为氢原子或卤素原子，或羟基、可选取代的烷基、可选取代的环烷基、可选取代的环烷基烷基、可选取代的芳基烷基、可选取代的杂芳基烷基、可选取代的芳氧基烷基、可选取代的杂芳氧基烷基、可选取代的烯基、可选取代的炔基、可选取代的芳基、可选取代的杂芳基、可选取代的烷氧基、可选取代的芳基烷氧基、可选取代的芳氧基、可选取代的杂芳氧基、可选取代的酰氧基、可选取代的氨基、可选取代的酰胺基、可选取代的芳基偶氮基、硝基、氰基、-CO2R6、-CONR7R8、-COR9-CR=NR10、-CR=NO R10或-N=CR11R12基团；或当它们在环上相邻的位置时，X和Y可以选择连接成为融合环，可以是芳香环或脂环，可以含有一个或多个杂原子；R、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12相同或不同，为氢原子（只要R4和R5不是氢原子），或可选取代的烷基、可选取代的环烷基、可选取代的环烷基烷基、可选取代的芳基烷基、可选取代的杂芳基烷基、可选取代的芳氧基烷基、可选取代的杂芳氧基烷基、可选取代的烯基、可选取代的炔基、可选取代的芳基或可选取代的杂芳基团；以及它们的金属络合物。这些化合物在农业中有用，特别是作为杀菌剂，也可以作为杀虫剂和植物生长调节剂。
• Fungicides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0243014B1

  公开（公告）日：1991-03-06
• 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.