(4-methoxyphenyl)phenylphosphine oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-methoxyphenyl)phenylphosphine oxide
• 英文别名: phenyl(4-methoxyphenyl)phosphine oxide；1-Methoxy-4-phenylphosphonoylbenzene；1-methoxy-4-phenylphosphonoylbenzene
• 化学式: C₁₃H₁₃O₂P
• 分子量: 232.219
• InChiKey: CQGBFMMLGHGFSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)phenylphosphine oxide 以 四氢呋喃 为溶剂， 反应 75.03h， 生成 p-anisyl(1-hydroxy-1-methylethyl)phenylphosphine borane
  参考文献：
  名称：

  Reduction of Functionalized Tertiary Phosphine Oxides with BH₃

  摘要：

  A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphineboranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O center dot center dot center dot B complexation directed by proximal alpha- or beta-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.

  DOI：

  10.1021/jo502623g
• 作为产物：
  描述：

  苯基二氯化磷 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 (4-methoxyphenyl)phenylphosphine oxide
  参考文献：
  名称：

  可见光诱导的配体到金属电荷转移的激发使芳基卤化物的磷酸化成为可能

  摘要：

  我们在此描述了可见光诱导的仲膦氧化物与芳基卤化物的镍（II）催化的交叉偶联。Ni （I）物种和氯原子自由基Cl˙是通过NiCl 2（PPh 3）2的配体到金属电荷转移（LMCT）过程生成的，该过程允许就地形成镍（IV） -磷物种，从而产生多种在无光催化剂的条件下生成叔膦氧化物。

  DOI：

  10.1039/d1cc01858b

文献信息

• Phosphinyl Guanidine Compounds, Metal Salt Complexes, Catalyst Systems, and Their Use to Oligomerize or Polymerize Olefins
  申请人：SYDORA Orson J.

  公开号：US20130331629A1

  公开（公告）日：2013-12-12

  The present application relates to N 2 -phosphinyl guanidine metal salt complexes. The present application also relates to catalyst systems comprising N 2 -phosphinyl guanidine metal salt complexes and processes for making catalyst systems comprising N 2 -phosphinyl guanidine metal salt complexes. The present application also relates to utilizing N 2 -phosphinyl guanidine metal salt complexes in processes of oligomerizing or polymerizing olefins.

  本申请涉及N2-磷酰亚胺基胍金属盐配合物。本申请还涉及包含N2-磷酰亚胺基胍金属盐配合物的催化剂体系以及制备包含N2-磷酰亚胺基胍金属盐配合物的催化剂体系的方法。本申请还涉及在烯烃的齐聚或聚合过程中利用N2-磷酰亚胺基胍金属盐配合物。
• Visible Light-Mediated Photocatalytic Metal-Free Cross-Coupling Reaction of Alkenyl Carboxylic Acids with Diarylphosphine Oxides Leading to β-Ketophosphine Oxides
  作者：Hai-Feng Qian、Cheng-Kun Li、Zhi-Hao Zhou、Ze-Kun Tao、Adedamola Shoberu、Jian-Ping Zou

  DOI：10.1021/acs.orglett.8b02639

  日期：2018.9.21

  A new visible light-mediated photocatalytic decarboxylative oxyphosphorylation of cinnamic acids with diarylphosphine oxides is described. This reaction is performed under mild conditions to afford the corresponding β-ketophosphine oxides.

  描述了一种新的可见光介导的肉桂酸与二芳基膦氧化物的光催化脱羧氧基磷酸化。该反应在温和的条件下进行，得到相应的β-酮膦氧化物。
• Synthesis of Organophosphorus Compounds through Copper-Catalyzed Annulation Involving C–O and C–P Bond Formations
  作者：Xue-Song Li、Ya-Ping Han、Xin-Yu Zhu、Ming Li、Wan-Xu Wei、Yong-Min Liang

  DOI：10.1021/acs.joc.7b01947

  日期：2017.11.3

  high-efficiency, and atom-economical synthesis of valuable organophosphorus compounds via cascade annulation of propargylic alcohols with diphenylphosphine oxide is described. This protocol, which has a good functional-group compatibility and insensitivity to an ambient atmosphere, provides a simple and direct pathway to the products, organophosphorus compounds, in good yields under mild conditions. The method

  描述了一种新颖的三氟甲磺酸铜（II）催化的高效炔烃与二苯基膦氧化物的级联环氧化合成有价值的有机磷化合物的方法。该方案对环境气氛具有良好的官能团相容性和不敏感性，可在温和条件下以高收率提供一条简单直接的途径通往有机磷化合物产品。该方法可以有效地放大到克级，从而突出了该方法的潜在应用。
• Zinc-catalyzed regioselective C–P coupling of <i>p</i>-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols
  作者：Ming Zhang、Xiaoyu Jia、Haowei Zhu、Xutong Fang、Chenyi Ji、Sizhuo Zhao、Li-Biao Han、Ruwei Shen

  DOI：10.1039/c9ob00129h

  日期：——

  regioselective C–P cross coupling reaction of p-quinol ethers with secondary phosphine oxides is reported. The reaction provides a facile alternative method for the synthesis of 2-phosphinylphenols in good to high yields. Mechanistically, zinc triflate may serve as an oxophilic σ-Lewis acid to activate the C–O bond in p-quinol ether first. Then the regioselective attack of the phosphorus nucleophile at the α-carbon

  据报道，三氟甲磺酸锌催化对苯二酚醚与仲氧化膦的高度区域选择性C–P交叉偶联反应。该反应为以高产率到高产率合成2-次膦酰基苯酚提供了一种简便的替代方法。机械地，三氟甲磺酸锌可以用作亲氧性σ的路易斯酸来激活在C-O键p -quinol醚第一。然后，磷亲核体在α-碳位置发生区域选择性攻击，形成C–P键并生成产物。另外，在锌催化剂的存在下，α-炔基取代的对苯二酚醚也以相同的反应模式与仲膦氧化物反应，得到6-炔基2-膦基苯酚。
• Z-Selective Addition of Diaryl Phosphine Oxides to Alkynes via Photoredox Catalysis
  作者：Huamin Wang、Yongli Li、Zilu Tang、Shengchun Wang、Heng Zhang、Hengjiang Cong、Aiwen Lei

  DOI：10.1021/acscatal.8b02617

  日期：2018.11.2

  Radical addition to alkynes is known to predominantly yield thermodynamically more stable E-alkenes. Control of stereoselectivity in these reactions, and the isolation of the higher-energy Z-alkenes, remain an important challenge in chemical synthesis. Herein, direct synthesis of Z-alkenylphosphine oxides via visible-light-induced radical addition to alkynes in water is reported. This protocol was

  已知向炔烃中自由基加成主要产生热力学上更稳定的E-烯烃。这些反应中立体选择性的控制以及高能Z-烯烃的分离仍然是化学合成中的重要挑战。本文中，报道了通过可见光诱导的自由基加成至水中的炔烃直接合成Z-烯基膦氧化物。该方案对各种末端和内部炔烃均有效，可提供具有高Z-立体选择性的产物。此外，这种转化以克为单位进行了证明。机理研究支持以下结论：（1）通过自由基加成反应。（2）K 2 CO 3的选择因为水性碱对转化至关重要；（3）π–π堆积相互作用极大地提高了Z选择性。