10-phenylbenzo[b]phosphindolo[2,3-d]thiophene 10-oxide | 1263143-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 10-phenylbenzo[b]phosphindolo[2,3-d]thiophene 10-oxide
• 英文别名: 10-Phenylphosphindolo[3,2-b][1]benzothiole 10-oxide；10-phenylphosphindolo[3,2-b][1]benzothiole 10-oxide
• CAS: 1263143-06-1
• 化学式: C₂₀H₁₃OPS
• 分子量: 332.362
• InChiKey: SKABLHPIYUXNSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-phenylbenzo[b]phosphindolo[2,3-d]thiophene 10-oxide 在 三氯硅烷 作用下， 以 苯 为溶剂， 反应 3.0h， 以68%的产率得到10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophene
  参考文献：
  名称：

  JP5780624

  摘要：

  公开号：
• 作为产物：
  描述：

  2-溴苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 溴 、 二乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.58h， 生成 10-phenylbenzo[b]phosphindolo[2,3-d]thiophene 10-oxide
  参考文献：
  名称：

  JP5780624

  摘要：

  公开号：

文献信息

• Synthesis of (Thio)Furan-Fused Phospholes via Phosphonation Cyclization and a Base-Promoted Phospha-Friedel–Crafts Reaction
  作者：Chenchen Li、Haiyang Huang、Fen Liu、Chengxiong Yuan、Siyu Chen、Yuhui Hua、Haixin Ding、Xian-Rong Song、Qiang Xiao

  DOI：10.1021/acs.joc.1c02577

  日期：2022.3.4

  strategy for synthesizing ladder (thio)furan-fused phospholes via intermolecular phosphonation cyclization and a base-promoted phospha-Friedel–Crafts reaction under mild conditions. The starting substrates are readily available phosphinic acids and easy-to-handle alkynes. The details of the reaction mechanism were further rationalized using theoretical calculations. This protocol can be widely applied to

  在此，我们开发了一种在温和条件下通过分子间磷酸化环化和碱基促进的磷酸-弗里德尔-克拉夫茨反应合成梯状（硫代）呋喃稠合磷酸酯的新策略。起始底物是容易获得的次膦酸和易于处理的炔烃。使用理论计算进一步合理化了反应机理的细节。该协议可广泛应用于合成呋喃和硫代呋喃稠合磷酸酯以及相应的大 π 扩展衍生物，这些衍生物在有机功能材料领域具有重要意义。
• Direct Synthesis of Dibenzophospholes from Biaryls by Double C–P Bond Formation via Phosphenium Dication Equivalents
  作者：Kazutoshi Nishimura、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.orglett.0c00944

  日期：2020.4.17

  the generation of phosphenium dication equivalents from readily available phosphinic acids and Tf2O. The in situ-generated dication equivalents can be readily coupled with simple (hetero)biaryls to form the corresponding dibenzophospholes directly. This protocol can also be applied to the concise synthesis of six- and seven-membered phosphacycles as well as the largely π-extended heteroacene derivatives

  我们已经开发了一种新的策略，用于从易于获得的次膦酸和Tf 2 O生成正当当量。原位生成的正当当量可轻松与简单的（杂）联芳基偶合，直接形成相应的二苯并膦。该方案也可用于六元和七元磷环的简捷合成以及大部分π延伸的杂并苯衍生物，这些在有机功能材料领域非常重要。
• Synthesis of Dibenzophospholes by Tf₂O-Mediated Intramolecular Phospha-Friedel–Crafts-Type Reaction
  作者：Kazutoshi Nishimura、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.orglett.9b00219

  日期：2019.3.1

  A Tf2O-mediated intramolecular phospha-Friedel–Crafts-type reaction of secondary biarylphosphine oxides has been developed. The reaction is promoted simply by Tf2O to form the corresponding dibenzophospholes under metal-free conditions. The starting substrates are readily available and easy-to-handle phosphine oxides, and the regioselectivity is controlled by the innate electronic nature. Thus, this

  二次联芳基膦氧化物的Tf 2 O介导的分子内膦-弗里德尔-克来福特型反应已得到开发。在没有金属的条件下，Tf 2 O可以简单地促进反应形成相应的二苯并膦。起始底物容易获得且易于处理的氧化膦，并且区域选择性由固有的电子性质控制。因此，该新开发的方案可以为材料化学中具有浓厚兴趣的高度π共轭二苯并膦提供简明和互补的方法。
• Ladder-Type <i>P</i>,<i>S</i>-Bridged <i>trans</i>-Stilbenes
  作者：Wannes Weymiens、Mark Zaal、J. Chris Slootweg、Andreas W. Ehlers、Koop Lammertsma

  DOI：10.1021/ic201116p

  日期：2011.9.5

  Phosphole-containing pi-systems have emerged as building blocks with enormous potential as electronic materials because of the tunability of the phosphorus center. Among these, asymmetric P-bridged trans-stilbenes are still rare, and here an elegant and efficient synthesis toward such fluorescent molecular frameworks is described. Fine-tuning of the photophysical properties is attempted by enforcing the planarization of the phosphorus tripod and thus increasing the interaction between the phosphorus lone pair and the pi-system, The electronic structure of the pi-conjugated frameworks is analyzed with NMR, UV-vis and fluorescence spectroscopy, and time-dependent density functional theory (TD-DFT) calculations.
• Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P−S System
  作者：Yi Ren、Thomas Baumgartner

  DOI：10.1021/ja108081b

  日期：2011.2.9

  New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of the materials' properties by exploitation of the different reactivities between sulfur and phosphorus. P-31 NMR. spectroscopy and X-ray crystallographic studies revealed that the different electronic effects of the secondary heteroatom, sulfur, influence not only the conjugation in the heterotetracene core but also the behavior of the phosphorus center. UV-vis and fluorescence spectroscopy showed that the scaffold's band gap is mainly controlled by the electronic nature of sulfur, while the fluorescence quantum yield highly depends on the electronic nature of phosphorus. Cyclic voltammetry indicated that the redox properties of the system could be altered by selective modification of the respective heteroatom (oxidation of sulfur and/or functionalization of trivalent phosphorus). Importantly, oxidation of the phosphorus center results in enhanced reduction features of the heterotetracene system, and oxidation of the sulfur center further enhances the electron acceptor character of the core. Theoretical calculations provided insights on both selectivity of phosphorus chemistry and communication between the two heteroatoms (sulfur and phosphorus). Macroscopic self-organization of the heterotetracenes was observed when the tetracene core is functionalized with pendant functional groups. Preliminary results showed that extension of the molecule with an alkyl chain along the long axis of molecules induces the formation of ID microfibers, which was confirmed by fluorescence microscopy and scanning electron microscopy.