anthracen-9-yldiphenylphosphane | 110954-35-3

• 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: anthracen-9-yldiphenylphosphane
• 英文别名: (9-Anthracenyl)diphenylphosphine；anthracen-9-yl(diphenyl)phosphane
• CAS: 110954-35-3
• 化学式: C₂₆H₁₉P
• 分子量: 362.411
• InChiKey: QHILUGXSOQKIPI-UHFFFAOYSA-N

物化性质

• 熔点：
  203.5 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  525.9±19.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  anthracen-9-yldiphenylphosphane 在 selenium 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以92%的产率得到C₂₆H₁₉PSe
  参考文献：
  名称：

  Synthesis, spectroscopy, electrochemistry, and coordination chemistry of substituted phosphine sulfides and selenides

  摘要：

  Phosphines and phosphine chalcogenides are important ligands for various metal systems, especially catalysts. Based on previously synthesized phosphine oxide ligands, we describe here the synthesis and characterization of a series of compounds having the general formula, EPPh2Ar, E = S, Se; Ar = 1-naphthyl, 9-phenanthryl, 9-anthracenyl, 1-pyrenyl. Reaction of EPPh2(9-phenanthryl), E = S, Se, with HAuCl4 yields ArPh2PEAuCl. Similar to the phosphine oxide derivative, the anthracenyl compounds, EPPh2(9-anthracenyl), showed a nonplanar conformation within the anthracene ring as observed using X-ray crystallography. The difference in fluorescence spectrum relative to the parent aryl species is attributed to this deformation. The deviation is probably due to steric strain within the phosphine ligand due to its position on the anthracenyl ring since OFT calculations suggest that the 1-anthracenyl ligand should be planar. Each compound has been characterized using H-1, C-13, P-31, and (where applicable) Se-77 NMR, and IR spectroscopy, with structure determination by X-ray crystallography. Finally, the electrochemistry of the unoxidized phosphines is reported, showing one-electron reductions in the polycyclic aromatic hydrocarbons. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.07.008
• 作为产物：
  描述：

  9-溴蒽 、 二苯基氯化膦 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.84h， 生成 anthracen-9-yldiphenylphosphane
  参考文献：
  名称：

  通过主客体复合物形成对取代蒽的固态发光发射放大进行分析。

  摘要：

  显示出固态发光的小而坚固的有机分子是光电材料的有希望的候选者。在此，我们研究了一系列二苯基膦酰蒽[9-PPh 2 ‐10-R-(C 14 H 8 )]及其硫氧化类似物。氧化导致分子结构发生巨大变化，因为大体积 (S)PPh 2取代基的新取向诱导了蒽核的强烈蝶形弯曲结构，从而引发了强烈的红移，从而产生绿色固态荧光。由于发射特性在聚集时仅发生轻微变化，因此发射的起源归因于典型的单体荧光。[9-(S)PPh 2 ‐10-乙基-(C 14 H 8 )]与四种基本芳烃的主客体复合物显示出与纯主体相比，发射增强高达五倍的量子产率。由于与共结晶芳烃的弱 C−H⋅⋅⋅π 相互作用的固定，发色团间相互作用较少，并且主体分子内分子内运动受到限制，这是导致发射增强的原因。

  DOI：

  10.1002/chem.202003017

文献信息

• 9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes
  作者：Minori Shimizu、Tetsuya Yamamoto

  DOI：10.1016/j.tetlet.2020.152257

  日期：2020.8

  9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes such asα,β-unsaturated ketones, esters, nitrile and nitroalkenes gave corresponding β-arylated alkanes in good yields and achieved TON up to 700.

  9-（二苯基膦基）蒽基的磷环戊四环催化将芳基硼酸共轭加成到缺电子的烯烃上，例如α，β-不饱和酮，酯，腈和硝基烯烃，以良好的收率得到了相应的β-芳基烷烃，TON达到700。
• Synthesis of <i>peri</i>-Substituted (Naphthalen-1-yl)phosphine Ligands by Rhodium(I)-Catalyzed Phosphine-Directed C–H Arylation
  作者：Xue Luo、Jia Yuan、Chang-Duo Yue、Zi-Yang Zhang、Jian Chen、Guang-Ao Yu、Chi-Ming Che

  DOI：10.1021/acs.orglett.8b00305

  日期：2018.4.6

  A novel protocol for effective rhodium(I)-catalyzed C–H arylation of tertiary phosphines has been devised. It is amenable to a wide range of substrates and gives the products in moderate to high yields. This strategy provides a simple and efficient route to peri-substituted (naphthalen-1-yl)phosphines.

  已经设计出有效的铑（I）催化叔膦的CH芳基化的新协议。它适用于各种基材，并能以中等到高产量提供产品。该策略提供了一种简单而有效的路线周围取代的（萘-1-基）膦。
• Remote C5-Selective Functionalization of Naphthalene Enabled by P–Ru–C Bond-Directed δ-Activation
  作者：Yueliuting Fu、Cui-Hong Chen、Mao-Gui Huang、Jun-Yang Tao、Xu Peng、Hai-Bing Xu、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1021/acscatal.2c00839

  日期：2022.5.6

  and aldehyde) in the C5 position with excellent regioselectivity (C5/others >20:1). Moreover, this protocol is also suitable for polycyclic aromatic hydrocarbons and the more remote C8 position. Preliminary mechanistic studies show that the tertiary phosphine group plays two essential roles in the reaction: first, it assists the introduction of Ru–C bond at the C8 position; second, due to the induction

  在萘衍生物的邻位、间位和对位之外进行位点选择性功能化非常具有挑战性，尤其是对于相邻苯环对位的远程 C5 位置。在此，我们报告了萘的远程 C5 选择性功能化叔膦诱导的钌催化的δ键活化。该策略超越了传统的位点选择性，有效地将不同的官能团（烷基、氟烷基和醛）安装在 C5 位置，具有出色的区域选择性（C5/其他 >20:1）。此外，该协议还适用于多环芳烃和更偏远的 C8 位置。初步机理研究表明，叔膦基团在反应中起两个重要作用：第一，它有助于在 C8 位引入 Ru-C 键；其次，由于诱导效应，它通过形成供电子的 P-Ru-C 键来辅助 δ 键的活化。
• Complexes of gold(I) and platinum(II) with polyaromatic phosphine ligands
  作者：Thomas E Müller、Jennifer C Green、D.Michael P Mingos、C.Mary McPartlin、Conrad Whittingham、David J Williams、Thomas M Woodroffe

  DOI：10.1016/s0022-328x(97)00522-6

  日期：1998.1

  Gold and platinum(II) complexes of the phosphine ligands PArnPh3−n (Ar=naphthyl, anthracenyl, ferrocenyl and other polyaromatic groups) have been synthesised. The electron donating abilities of naphthyl and anthracenyl phosphine ligands has been explored using gas phase photoelectron spectral data on the parent phosphines and their relative complexing ability to platinum precursor molecules has been

  已经合成了膦配体PAr n Ph 3- n（Ar =萘基，蒽基，二茂铁基和其他多芳族基团）的金和铂（II）配合物。已使用有关母体膦的气相光电子光谱数据探索了萘基和蒽基膦配体的给电子能力，并通过合成研究和NMR实验评估了它们与铂前体分子的相对络合能力。通过使用X射线晶体学数据的托尔曼锥角方法估计了它们的空间参数。金络合物[AuCl（PAn 2 Ph）]·CHCl 3和[Au（PFc 2 Ph）2 ]·CHCl的分子结构3个已经确定。
• Functionalized silicate nanoparticle composition, removing and exfoliating asphaltenes with same
  申请人：Baker Hughes Incorporated

  公开号：US10703959B2

  公开（公告）日：2020-07-07

  Removing an asphaltene particle from a substrate includes contacting a silicate nanoparticle with a chemical group to form a functionalized silicate nanoparticle, the chemical group includes a first portion; and a second portion comprising a nonaromatic moiety, the first portion being bonded to the silicate nanoparticle; contacting the asphaltene particle with the functionalized silicate nanoparticle, the asphaltene particle being disposed on the substrate; interposing the functionalized silicate nanoparticle between the asphaltene particle and the substrate; and separating the asphaltene particle from the substrate with the functionalized silicate nanoparticle to remove the asphaltene particle. A composition includes a functionalized silicate nanoparticle comprising a reaction product of a silicate nanoparticle and a functionalization compound; and a fluid. The functionalization compound includes a chemical group that includes a first portion, the first portion being directly bonded to the silicate nanoparticle in the functionalized silicate nanoparticle; and a second portion including an aromatic moiety or a nonaromatic moiety.

  从基质中去除沥青质颗粒包括将硅酸盐纳米颗粒与化学基团接触以形成官能化硅酸盐纳米颗粒，化学基团包括第一部分；以及包括非芳香族分子的第二部分，第一部分与硅酸盐纳米颗粒结合；将沥青质颗粒与官能化硅酸盐纳米颗粒接触，沥青质颗粒置于基底上；将官能化硅酸盐纳米颗粒置于沥青质颗粒和基底之间；以及用官能化硅酸盐纳米颗粒将沥青质颗粒与基底分离，以除去沥青质颗粒。一种组合物包括官能化硅酸盐纳米粒子，该纳米粒子包括硅酸盐纳米粒子和官能化化合物的反应产物；以及流体。官能化化合物包括一个化学基团，该基团包括第一部分，第一部分直接与官能化硅酸盐纳米粒子中的硅酸盐纳米粒子结合；以及第二部分，包括芳香族分子或非芳香族分子。