10-phenylbenzophospholo[3,2-b]benzofuran oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 10-phenylbenzophospholo[3,2-b]benzofuran oxide
• 英文别名: 10-phenyl-10-oxo-[1]benzophospholo[3,2-b][1]benzofuran；10-Phenylphosphindolo[3,2-b][1]benzofuran 10-oxide；10-phenylphosphindolo[3,2-b][1]benzofuran 10-oxide
• 化学式: C₂₀H₁₃O₂P
• 分子量: 316.296
• InChiKey: GZRMAFSURHNXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-phenylbenzophospholo[3,2-b]benzofuran oxide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以95%的产率得到10-phenylbenzophospholo[3,2-b]benzofuran sulfide
  参考文献：
  名称：

  Synthesis and Properties of Benzophospholo[3,2-b]benzofuran Derivatives

  摘要：

  Benzophospholo[3,2-b]benzofuran (BPBF) derivatives were studied as a new family of phosphole-containing p-conjugated organic materials. The versatile reactivity of the trivalent phosphorus center of the parent BPBF offered access to a variety of derivatives by simple chemical modifications. The diversity-oriented synthetic route was also developed to allow facile access to BPBFs with a different substituent on the phosphorus center. Photophysical properties were revealed based on UV-vis and photoluminescence spectroscopies and theoretical calculation. The characteristic property of BPBF derivatives is highly efficient photoluminescence. In particular, phosphole oxide derivatives demonstrated intense blue fluorescence with high quantum yield over 85% even in the solid state.

  DOI：

  10.1021/jo502889r
• 作为产物：
  描述：

  2-溴苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 碘 、 二乙胺 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 50.25h， 生成 10-phenylbenzophospholo[3,2-b]benzofuran 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。
• Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties
  作者：Chenchen Li、Haiyang Huang、Longgen Sun、Mingqing Huang、Haixin Ding、Jiang Bai、Ban‐Peng Cao、Qiang Xiao

  DOI：10.1002/anie.202215436

  日期：2023.2

  Herein, we report a straightforward three-component synthesis of novel dioxaphosphorane-fused diphosphacycles with distinctive photophysical properties. Based on their unique structure and properties, a novel fluorescent switch for pH sensing was revealed by a dynamic ring-opening/ring-closing mechanism.

  在此，我们报告了具有独特光物理特性的新型二氧杂正膦稠合二磷酸环的直接三组分合成。基于其独特的结构和特性，通过动态开环/闭环机制揭示了一种用于 pH 传感的新型荧光开关。