3-(methylselanyl)-2-phenylbenzofuran | 1191950-92-1

• 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: 3-(methylselanyl)-2-phenylbenzofuran
• 英文别名: 3-Methylselanyl-2-phenyl-1-benzofuran
• CAS: 1191950-92-1
• 化学式: C₁₅H₁₂OSe
• 分子量: 287.22
• InChiKey: XPHYHVKIJPMJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二甲基二硒醚 、 1-甲氧基-2-苯基乙炔-苯 在 碘 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以59%的产率得到3-(methylselanyl)-2-phenylbenzofuran
  参考文献：
  名称：

  通过碘介导的2-炔基苯甲醚的亲电子环化反应，无金属合成3-硫属元素苯并[ b ]呋喃

  摘要：

  通过用二硫化物或二硒化物通过碘介导的2-炔基茴香醚的亲电亲电环化反应，开发了一种高效且无金属的方法来合成3-硫属元素苯并[ b ]呋喃。在I 2的存在下，以中等至高产率获得了各种3-亚磺酰基苯并呋喃或3-硒代苯并呋喃。

  DOI：

  10.1016/j.tetlet.2011.10.045

文献信息

• Metal-free synthesis of 3-chalcogen benzo[b]furans via an iodine-mediated electrophilic cyclisation of 2-alkynylanisoles
  作者：Mei Xu、Xiao-Hong Zhang、Ping Zhong

  DOI：10.1016/j.tetlet.2011.10.045

  日期：2011.12

  An efficient and metal-free method was developed to synthesize 3-chalcogen benzo[b]furans via the iodine-mediated electrophilic cyclisation of 2-alkynylanisoles with disulfides or diselenides. In the presence of I2, various 3-sulfenylbenzofurans or 3-selenenylbenzofurans were obtained in moderate to high yields.

  通过用二硫化物或二硒化物通过碘介导的2-炔基茴香醚的亲电亲电环化反应，开发了一种高效且无金属的方法来合成3-硫属元素苯并[ b ]呋喃。在I 2的存在下，以中等至高产率获得了各种3-亚磺酰基苯并呋喃或3-硒代苯并呋喃。
• PdCl₂-Promoted Electrophilic Annulation of 2-Alkynylphenol Derivatives with Disulfides or Diselenides in the Presence of Iodine
  作者：Hui-Ai Du、Xing-Guo Zhang、Ri-Yuan Tang、Jin-Heng Li

  DOI：10.1021/jo9016309

  日期：2009.10.16

  of 3-chalcogen-benzo[b]furans via palladium-promoted annulation reactions of 2-alkynylphenol derivatives with disulfides or diselenides and iodide has been developed. In the presence of I2 and PdCl2, both 3-sulfenylbenzofurans and 3-selenenylbenzofurans were selectively prepared from the cyclization of 2-alkynyanisoles with disulfides or diselenides in moderate to excellent yields.

  通过2-炔基苯酚衍生物与二硫化物或二硒化物和碘化物的钯促进的环化反应，已开发出有效合成3-硫属元素-苯并[ b ]呋喃的方法。在I 2和PdCl 2的存在下，由2-炔基吲哚与二硫化物或二硒化物的环化反应选择性地制备了3-亚磺酰基苯并呋喃和3-硒烯苯并呋喃，且产率中等至优异。
• 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, 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。