2-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)benzofuran | 1238892-16-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)benzofuran
• 英文别名: 2-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)benzo[b]furan；2-Phenyl-3-[3-(trifluoromethyl)phenyl]selanyl-1-benzofuran
• CAS: 1238892-16-4
• 化学式: C₂₁H₁₃F₃OSe
• 分子量: 417.289
• InChiKey: HZRLRMCRGNGHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Selectfluor 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 2-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)benzofuran
  参考文献：
  名称：

  SelectFluor® 促进 3-硒基苯并[b]呋喃的合成

  摘要：

  开发了一种简单实用的由 SelectFluor® 试剂介导的3-硒基-苯并[ b ]呋喃合成方案。这种新颖的方法提供了一种在温和条件下通过无金属程序生成 3-取代-苯并[ b ]呋喃的更环保的替代方案。分子内环化反应采用通过 SelectFluor® 和有机二硒化物之间的反应原位产生的亲电硒物质进行。通过异核核磁共振波谱证实了这种亲电硒物质（RSe-F）的形成，并探讨了其反应性。

  DOI：

  10.1039/d0ra01907k

文献信息

• FeCl₃-Diorganyl Dichalcogenides Promoted Cyclization of 2-Alkynylanisoles to 3-Chalcogen Benzo[<i>b</i>]furans
  作者：Rafaela M. Gay、Flávia Manarin、Caroline C. Schneider、Daniela A. Barancelli、Michael D. Costa、Gilson Zeni

  DOI：10.1021/jo101126q

  日期：2010.8.20

  2-alkynylanisoles, via FeCl3/diorganyl dichalcogenides intramolecular cyclization, has been developed. Aryl and alkyl groups directly bonded to the chalcogen atom were used as cycling agents. The results revealed that the reaction significantly depends on the electronic effects of substituents in the aromatic ring bonded to the selenium atom of the diselenide species. We observed that the pathway of reaction was

  通过FeCl 3从容易获得的2-炔基苯甲醚中合成3-硫属元素苯并[ b ]呋喃/ diorganyl dichalcogenides分子内环化已得到开发。直接结合到硫属元素原子上的芳基和烷基用作循环剂。结果表明，该反应显着取决于与二硒化物物种的硒原子键合的芳环中取代基的电子效应。我们观察到反应途径对苯甲醚芳环中取代基的性质不敏感，因为给电子基团和吸电子基团均以相似的产率传递产物。此外，将得到的杂环被容易地通过使用与硫属/锂交换反应转化成更复杂的产品Ñ-BuLi，然后用醛截留锂中间体，以良好的产率提供所需的仲醇。
• Trichloroisocyanuric Acid (TCCA): A Suitable Reagent for the Synthesis of Selanyl‐benzo[ <i>b</i> ]chalcogenophenes
  作者：Gustavo B. Blödorn、Luis Fernando B. Duarte、Juliano A. Roehrs、Márcio S. Silva、José S. S. Neto、Diego Alves

  DOI：10.1002/ejoc.202200775

  日期：2022.10.26

  A new protocol for the synthesis of different 3-organyl-benzo[b]chalcogenophenes was developed through the reaction of diorganyl diselenides with trichloroisocyanuric acid (TCCA) in ethanol. Under the optimized reaction conditions, a range of benzo[b]furans, benzo[b]thiophenes and benzo[b]selenophenes were synthesized in good to excellent yields using mild reaction conditions.

  通过二有机基二硒化物与三氯异氰脲酸 (TCCA) 在乙醇中的反应，开发了一种合成不同 3-有机基苯并[ b ]硫族酚的新方案。在优化的反应条件下，一系列苯并[ b ]呋喃、苯并[ b ]噻吩和苯并[ b ]硒吩类化合物在温和的反应条件下以良好至优异的收率合成。
• Synthesis, Characterizations, Crystal Structure, DFT, and Hirshfeld Surface Analysis of 4-Cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide
  作者：Shivendra Kumar Pandey、Seema Gupta、Shubham Jaiswal、M. K. Gond、M. K. Bharty、R. J. Butcher

  DOI：10.1007/s10870-022-00965-x

  日期：——

  The crystal structure of the thiosemicarbazide derivative 4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide (ChtcTSC), C12H17N3OS2, is reported here. The title compound ChtcTSC has been characterized by various physicochemical techniques viz UV–Vis., Infrared, and NMR. It crystallizes in the monoclinic system having space group P21/c. The dihedral angle between the thiophene and cyclohexyl rings is 60.7(4)°. The crystal packing is established by intermolecular N–H⋯O packing interactions involving a three-center donor hydrogen bond between the keto oxygen atom of the thiophene group and H atoms belonging to the hydrazine group which links the molecules into chains along the (011) plane of the unit cell. Hydrogen bonds between the hydrazine hydrogen atom and one of the thiophene groups and C–H⋯Cg π -ring interactions provide added stability to the crystal packing. The fingerprint plots associated with Hirshfeld surface analysis indicate that there are different types of weak interactions viz. O⋯H–C, O⋯H–N, and S⋯H–C. The geometry optimization has been performed using the DFT method, and geometrical parameters thus obtained for ChtcTSC correlate with the single-crystal X-ray data. The TD-DFT study showed a small HOMO and LUMO energy gap of 2.869 eV. The electronic transition from the ground state to the excited state due to a transfer of electrons from HOMO to LUMO levels is mainly associated with the n → π* transition. The crystal structure of 4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide (ChtcTSC) is reported here where the title compound ChtcTSC has been characterized by various physiochemical techniques including UV–Vis., Infrared, NMR, DFT and Hirshfeld surface analysis.

  本文报告了硫代氨基脲衍生物 4-环己基-1-(噻吩-2-羰基)硫代氨基脲（ChtcTSC）（C12H17N3OS2）的晶体结构。标题化合物 ChtcTSC 已通过紫外可见光、红外线和核磁共振等各种理化技术进行了表征。它在单斜体系中结晶，空间群为 P21/c。噻吩环和环己基环之间的二面角为 60.7(4)°。晶体的堆积是由分子间的 N-H⋯O 堆积相互作用形成的，其中涉及噻吩基团的酮氧原子和属于肼基团的 H 原子之间的三中心供体氢键，该氢键将分子沿单胞的 (011) 平面连接成链。肼氢原子和其中一个噻吩基团之间的氢键以及 C-H⋯Cg π - 环相互作用增加了晶体堆积的稳定性。与 Hirshfeld 表面分析相关的指纹图表明，存在不同类型的弱相互作用，即 O⋯H-C、O⋯H-N 和 S⋯H-C。使用 DFT 方法对 ChtcTSC 进行了几何优化，由此获得的几何参数与单晶 X 射线数据相关。TD-DFT 研究表明，该化合物的 HOMO 和 LUMO 能隙较小，分别为 2.869 eV 。由于电子从 HOMO 水平转移到 LUMO 水平，从基态到激发态的电子转变主要与 n → π* 转变有关。本文报告了 4-环己基-1-(噻吩-2-羰基)硫代氨基甲酰肼（ChtcTSC）的晶体结构，并通过紫外可见光、红外、核磁共振、DFT 和 Hirshfeld 表面分析等多种理化技术对标题化合物 ChtcTSC 进行了表征。
• Direct Electrooxidative Selenylation/Cyclization of Alkynes: Access to Functionalized Benzo[b]furans
  作者：Balati Hasimujiang、Shengsheng Lin、Chengwei Zheng、Yong Zeng、Zhixiong Ruan

  DOI：10.3390/molecules27196314

  日期：——

  A mild, practical, metal and oxidant-free methodology for the synthesis of various C-3 selenylated benzo[b]furan derivatives was developed through the intramolecular cyclization of alkynes promoted with diselenides via electrooxidation. A wide range of selenium-substituted benzo[b]furan derivatives were obtained in good to excellent yields with high regioselectivity under constant current in an undivided

  通过用二硒化物通过电氧化促进炔烃的分子内环化，开发了一种温和、实用、无金属和无氧化剂的方法，用于合成各种 C-3 硒化苯并[ b ]呋喃衍生物。在分别配备碳和铂板作为阳极和阴极的未分隔电池中，在恒定电流下以良好至优异的产率获得了范围广泛的硒取代的苯并[ b ]呋喃衍生物，具有高区域选择性。此外，收敛方法表现出良好的官能团耐受性，并且可以很容易地以良好的效率进行放大，从而从简单、容易获得的起始材料中快速获得各种硒化苯并[ b ]呋喃衍生物。
• Synthesis of 3-selanylbenzo[<i>b</i>]furans promoted by SelectFluor®
  作者：Maurício Carpe Diem Ferreira Xavier、Eduardo Martarelo Andia Sandagorda、José Sebastião Santos Neto、Ricardo Frederico Schumacher、Márcio Santos Silva

  DOI：10.1039/d0ra01907k

  日期：——

  A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor® reagent was developed. This novel methodology provided a greener alternative to generate 3-substituted-benzo[b]furans via a metal-free procedure under mild conditions. The intramolecular cyclization reaction was carried out employing an electrophilic selenium species generated in situ through

  开发了一种简单实用的由 SelectFluor® 试剂介导的3-硒基-苯并[ b ]呋喃合成方案。这种新颖的方法提供了一种在温和条件下通过无金属程序生成 3-取代-苯并[ b ]呋喃的更环保的替代方案。分子内环化反应采用通过 SelectFluor® 和有机二硒化物之间的反应原位产生的亲电硒物质进行。通过异核核磁共振波谱证实了这种亲电硒物质（RSe-F）的形成，并探讨了其反应性。