diphenyl(m-tolyl)phosphine oxide | 6840-27-3

• 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: diphenyl(m-tolyl)phosphine oxide
• 英文别名: Diphenyl-m-tolyl-phosphinoxid；m-Tolyl-diphenyl-phosphinoxid；(3-methylphenyl)diphenylphosphine oxide；Diphenyl-m-tolylphosphine oxide；1-diphenylphosphoryl-3-methylbenzene
• CAS: 6840-27-3
• 化学式: C₁₉H₁₇OP
• 分子量: 292.317
• InChiKey: JPOGITLPCPOLER-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  481.6±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  ethyl Phenylphosphinate 在 bis(triphenylphosphine)nickel(II) chloride 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 diphenyl(m-tolyl)phosphine 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

• Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds
  作者：Kaiqiang Xu、Long Liu、Zhaohui Li、Tianzeng Huang、Kang Xiang、Tieqiao Chen

  DOI：10.1021/acs.joc.0c01557

  日期：2020.11.20

  The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

  开发了可控制的硫酯磷酸化。当反应由钯催化剂催化时，当仅在碱的存在下进行反应时，芳基或烯基磷酰基化合物通过脱羰偶合产生，而苄基磷酰基化合物通过脱氧偶合产生。
• Copper‐Catalyzed C−P Cross‐Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with <i>in</i>   <i>situ</i> Halogen Exchange
  作者：Paweł Woźnicki、Marek Stankevič

  DOI：10.1002/ejoc.202100456

  日期：2021.6.25

  A protocol for copper-catalyzed halogen exchange/C−P cross-coupling between (cyclo)alkenyl/aryl bromides and secondary phosphine oxides has been developed. The addition of sodium iodide increases the yield of the cross-coupling by promoting in situ halogen exchange of organic bromides to the corresponding iodides.

  已经开发了用于（环）烯基/芳基溴化物和二级氧化膦之间的铜催化卤素交换/CP 交叉偶联的协议。碘化钠的添加通过促进有机溴化物与相应碘化物的原位卤素交换来增加交叉偶联的产率。
• Palladium-Catalyzed C–P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide
  作者：Holly McErlain、Leanne M. Riley、Andrew Sutherland

  DOI：10.1021/acs.joc.1c02172

  日期：2021.12.3

  iodide-accelerated, palladium-catalyzed C–P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward

  描述了芳基九氟磺酸盐的碘化物加速、钯催化 C-P 键形成反应。该方案针对芳基氧化膦的合成进行了优化，并且被发现能够耐受多种芳基九氟磺酸盐。这种转化的一般性质是通过与其他 P(O)H 化合物偶联来合成芳基膦酸酯和芳基次膦酸酯而建立的。稳定、可分离的芳基九氟磺酸盐的直接合成，与快速的 C-P 键形成反应相结合，可以从容易获得的苯酚起始材料中轻松制备芳基磷目标化合物。通过有机发光二极管（OLED）材料和膦酰基苯丙氨酸模拟物的有效制备，证明了该总体策略的合成效用。
• Aryl group – a leaving group in arylphosphine oxides
  作者：Marek Stankevič、Jolanta Pisklak、Katarzyna Włodarczyk

  DOI：10.1016/j.tet.2015.12.043

  日期：2016.2

  The treatment of triphenylphosphine oxide with organometallic reagents leads to the substitution of up to three phenyl substituents with the incoming carbon nucleophile. The replacement of the phenyl/aryl group in tertiary diarylalkylphosphine oxides or even aryldialkylphosphine oxides was also observed. Naphthyl-substituted phosphine oxides undergo Michael-type addition at the naphthyl group when

  用有机金属试剂处理三苯基氧化膦会导致最多三个苯基取代基被传入的碳亲核试剂取代。还观察到叔二芳基烷基膦氧化物或什至芳基二烷基膦氧化物中苯基/芳基的取代。当用有机锂试剂处理时，萘基取代的氧化膦在萘基上经历迈克尔型加成。
• Nickel-catalysed P–C bond formation via P–H/C–CN cross coupling reactions
  作者：Ji-Shu Zhang、Tieqiao Chen、Jia Yang、Li-Biao Han

  DOI：10.1039/c5cc01182e

  日期：——

  Nickel-catalysed P–H/C–CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp²C–P bonds. This transformation provides a convenient method for the preparation of both arylphosphines and arylphosphine oxides from the readily available P–H compounds and arylnitriles.

  镍催化的P-H/C-CN交叉偶联反应在温和的反应条件下高效进行，形成相应的sp2C-P键。这种转化为从易得的P-H化合物和芳基腈制备芳基膦和芳基膦氧化物提供了便捷的方法。