3-styrylthiophene | 35022-11-8

• 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-styrylthiophene
• 英文别名: 3-(2-Phenylethenyl)thiophene
• CAS: 35022-11-8
• 化学式: C₁₂H₁₀S
• 分子量: 186.277
• InChiKey: KLNYYUBWOQQZAE-UHFFFAOYSA-N

物化性质

• 沸点：
  294.4±15.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-styrylthiophene 以 乙腈 为溶剂， 以100%的产率得到dihydronaphtho-[1,2-b]thiophene
  参考文献：
  名称：

  Photocyclization and photooxidation of 3-styrylthiophene

  摘要：

  The photocyclization, dye-sensitized photooxidation and auto-photooxidation of 3-styrylthiophene have been examined, cis-3-Styrylthiophene undergoes photochemical cis-trans isomerization and cyclization to dihydronaphtho-[1,2-b]thiophene. The quantum efficiency for photocyclization in nonpolar solvents is greater than that in polar solvents. Dye-sensitized photooxidation of 3-styrylthiophene gives benzaldehyde and 3-thiophenecarboxaldehyde. This oxidation proceeds via a superoxide radical anion pathway rather than singlet oxygen pathway. In the presence of oxygen photoirradiation of 3-styrylthiophene solution results in photocyclization, oxidation and dimerization. The mechanism of the latter two reactions was described in terms of formation of a charge transfer complex between oxygen and the substrate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00097-6
• 作为产物：
  描述：

  diethyl 3-thenylphosphonate 、 苯甲醛 在 sodium hydride 作用下， 生成 3-styrylthiophene
  参考文献：
  名称：

  Tedjamulia, Marvin L.; Stuart, John G.; Tominaga, Yoshinori, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1215 - 1219

  摘要：

  DOI：

文献信息

• Copper-Catalyzed 8-Aminoquinoline-Directed Oxidative C–H/N–H Coupling for <i>N</i>-Arylation of Sulfoximines
  作者：Gowri Sankar Grandhi、Suman Dana、Anup Mandal、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.0c00545

  日期：2020.4.3

  A copper-catalyzed cross-dehydrogenative C–H/N–H coupling has been devised to access a series of N-arylated sulfoximines in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, and mechanistic studies favor the involvement of an organometallic pathway, where C–H bond cleavage is presumed to be the kinetically relevant step. The utility of sulfoximine-coupled

  已经设计了铜催化的交叉脱氢C–H / N–H偶联物，以从8-氨基喹啉衍生的苯甲酰胺和亚砜肟类中高收率获得一系列N-芳基化亚砜基。该反应是可扩展的，并且机理研究支持有机金属途径的参与，其中CH键的断裂被认为是动力学上相关的步骤。通过镍催化的苄基醇的无受体脱氢烯化反应显示出了亚砜亚胺偶联的苯甲酰胺的效用。
• Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis
  作者：R. Antonioletti、F. Bonadies、A. Ciammaichella、A. Viglianti

  DOI：10.1016/j.tet.2008.02.091

  日期：2008.5

  A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.

  已经建立了由氢氧化锂和三苯基苄基溴化promote促进的Wittig烯烃化反应的温和且实用的方法，用于合成对苯二酚和苯乙烯。实验条件允许芳族，杂芳族，不饱和和饱和脂族醛以高收率得到最终产物。
• Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions
  作者：P. Kocięcka、A.M. Trzeciak

  DOI：10.1016/j.apcata.2019.117243

  日期：2020.1

  The hydroarylation of terminal alkynes with sodium tetraphenylborate was performed in high yield within 3 h at room temperature in water, using palladium(II) complexes with imidazole ligands as catalysts. Under these conditions, differently substituted phenylacetylene substrates were converted to arylalkenes and aryl-substituted dienes. High conversion and excellent selectivity were achieved in the

  使用具有咪唑配体的钯（II）配合物在室温下于室温下于水中在3小时内以高收率将末端炔烃与四苯硼酸钠进行加氢芳基化反应。在这些条件下，将不同取代的苯乙炔底物转化为芳基烯烃和芳基取代的二烯。在炔醇与四苯硼酸钠的加氢芳基化反应中实现了高转化率和出色的选择性。在这些反应中仅形成一种产物，具有OH基的芳基烯烃，其产率取决于所用炔醇的种类。根据反应混合物中鉴定出的钯种类和H / D交换研究，提出了合理的加氢芳基化反应机理。证明了水作为氢化物来源的贡献。
• 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。
• Highly Active [Pd(μ‐Cl)Cl(NHC)] ₂ Complexes in the Mizoroki–Heck Reaction
  作者：Ulrike I. Tessin、Xavier Bantreil、Olivier Songis、Catherine S. J. Cazin

  DOI：10.1002/ejic.201300169

  日期：2013.4.12

  A series of Pd dimers bearing an N-heterocyclic carbene ligand was studied in the Mizoroki–Heck reaction. [Pd(μ-Cl)Cl(SIPr)]2 (SIPr = N,N′-bis[2,6-(diisopropyl)phenyl]imidazolidin-2-ylidene}) was shown to be highly efficient in this cross-coupling for a range of aryl and heterocyclic bromides, with low palladium loading (20–200 ppm).

  在 Mizoroki-Heck 反应中研究了一系列带有 N-杂环卡宾配体的 Pd 二聚体。[Pd(μ-Cl)Cl(SIPr)]2 (SIPr = N,N'-bis[2,6-(diisopropyl)phenyl]imidazolidin-2-ylidene}) 被证明在这种交叉中非常有效。偶联一系列芳基和杂环溴化物，钯负载量低（20-200 ppm）。