diphenyl((phenylsulfonyl)methyl)phosphine oxide | 94333-12-7

• 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((phenylsulfonyl)methyl)phosphine oxide
• 英文别名: [benzenesulfonylmethyl(phenyl)phosphoryl]benzene
• CAS: 94333-12-7
• 化学式: C₁₉H₁₇O₃PS
• 分子量: 356.382
• InChiKey: JOQBGSBDKFITDP-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  531.7±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  diphenyl((phenylsulfonyl)methyl)phosphine oxide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到C10H20O5
  参考文献：
  名称：

  磷系甲烷化钌配合物形成碳配合物与环金属化反应

  摘要：

  已合成并分离了用于过渡金属配合物的氧代磷酰基取代的甲烷化物配体系统，作为钠盐Na [Ph 2 P（O）–C（H）–SO 2Ph]。该配体具有已知能够分离亲核后期过渡金属卡宾配合物的结构成分。可以通过简单的盐复分解反应容易地获得相应的钌（苏木）氯离子络合物。然而，与先前报道的硫代和亚氨基磷酰基系的配体系统相反，氯配合物的脱卤化氢导致形成环金属化钌配合物而不是卡宾配合物。所有化合物均以溶液和固态表征。已经进行了其他密度泛函理论（DFT）研究，以阐明观察到的环金属化的机理，并阐明配体系统中不同P（V）基团对相应卡宾配合物的稳定性和反应性的影响。与PS或P N部分相比，O负责更轻松的CH活化。

  DOI：

  10.1016/j.jorganchem.2020.121235
• 作为产物：
  描述：

  甲基二苯基膦硫化物 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 生成 diphenyl((phenylsulfonyl)methyl)phosphine oxide
  参考文献：
  名称：

  Synthesis and Electronic Structure of Carbene Complexes Based on a Sulfonyl-Substituted Dilithio Methandiide

  摘要：

  The application of a sulfonyl-substituted dilithio methandiide in the synthesis of carbene complexes was examined. In all cases, the metal carbon interaction was found to be highly polar with only small pi-contribution. Hence, the stability of these complexes was found to greatly rely on the coordination ability of the side-arms supporting the metal carbon interaction. As such, the sulfonyl moiety allowed the isolation of a carbene complex with the oxophilic zirconium, which is the first of its kind bearing no (bis)phosphonium ligand framework. On the contrary, complexes with the late transition metals ruthenium and palladium were found to be more labile due to the facile decoordination of the sulfonyl moiety. This results in the opening of a reactive coordination site at the metal center and hence in further reactions such as cyclometalation or sulfur transfer from the thiophosphoryl moiety to the carbenic carbon atom.

  DOI：

  10.1021/om5001277

文献信息

• Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines
  作者：Marina Cardoso Dilelio、Teodoro S. Kaufman、Bernardo Almeida Iglesias、Claudio C. Silveira

  DOI：10.1016/j.dyepig.2021.109982

  日期：2022.2

  the latter also exhibited more red-shifted absorption spectra, and Stokes shifts in the range 6115–8170 cm−1 with weak dependence of solvent polarity. The sulfoxide and sulfones displayed more red-shifted spectra than the corresponding sulfides. The cyclic voltammograms of all derivatives exhibited a common pattern of reversible or quasi-reversible processes in the anodic region, related to the phenothiazine

  报道了 Wittig-Horner 介导的带有乙烯基硫化物和乙烯基硒化物基序的吩噻嗪的合成，这些基序连接到芳环或连接到杂环的中心氮原子，以及随后对其光物理和电化学性质的研究。这些化合物以几何异构体的混合物形式获得，产率良好至极好。为了完成这项研究，还从相应的氧化膦氧化物制备了一小组乙烯基亚砜和乙烯基砜衍生物。在不同极性的溶剂中检查了化合物的光物理性质，其中它们在紫外区域呈现吸收最大值，摩尔吸收系数与对称允许的 π-π* 电子跃迁兼容。杂环衍生物是荧光的。带有与杂环氮原子相连的乙烯基硫醚部分的化合物比带有与芳环键合的乙烯基硫属元素化物的吩噻嗪衍生物显示出的荧光强度较低；后者还表现出更多的红移吸收光谱，斯托克斯位移范围为 6115-8170 cm-1具有弱的溶剂极性依赖性。亚砜和砜比相应的硫化物显示出更多的红移光谱。所有衍生物的循环伏安图在阳极区域表现出与吩噻嗪单元相关的可逆或准可逆过程的共同模式。
• 1,2-Umlagerung von Phosphor zu Kohlenstoff
  作者：Heinrich Hellmann、Jörg Bader

  DOI：10.1016/s0040-4039(01)91683-1

  日期：1961.1
• Synthesis and Electronic Structure of Carbene Complexes Based on a Sulfonyl-Substituted Dilithio Methandiide
  作者：Julia Becker、Viktoria H. Gessner

  DOI：10.1021/om5001277

  日期：2014.3.10

  The application of a sulfonyl-substituted dilithio methandiide in the synthesis of carbene complexes was examined. In all cases, the metal carbon interaction was found to be highly polar with only small pi-contribution. Hence, the stability of these complexes was found to greatly rely on the coordination ability of the side-arms supporting the metal carbon interaction. As such, the sulfonyl moiety allowed the isolation of a carbene complex with the oxophilic zirconium, which is the first of its kind bearing no (bis)phosphonium ligand framework. On the contrary, complexes with the late transition metals ruthenium and palladium were found to be more labile due to the facile decoordination of the sulfonyl moiety. This results in the opening of a reactive coordination site at the metal center and hence in further reactions such as cyclometalation or sulfur transfer from the thiophosphoryl moiety to the carbenic carbon atom.
• Carbene complex formation versus cyclometallation from a phosphoryl-tethered methanide ruthenium complex
  作者：Kai-Stephan Feichtner、Florian Papp、Michelle Schmidt、Maurice Paaßen、Viktoria H. Gessner

  DOI：10.1016/j.jorganchem.2020.121235

  日期：2020.6

  the isolation of nucleophilic late transition metal carbene complexes. The corresponding ruthenium(cymene) chlorido complex was readily available by simple salt metathesis reaction. However, in contrast to previously reported thio- and iminophosphoryl-tethered ligand systems, dehydrohalogenation of the chlorido complex led to the formation of a cyclometallated ruthenium complex instead of the carbene

  已合成并分离了用于过渡金属配合物的氧代磷酰基取代的甲烷化物配体系统，作为钠盐Na [Ph 2 P（O）–C（H）–SO 2Ph]。该配体具有已知能够分离亲核后期过渡金属卡宾配合物的结构成分。可以通过简单的盐复分解反应容易地获得相应的钌（苏木）氯离子络合物。然而，与先前报道的硫代和亚氨基磷酰基系的配体系统相反，氯配合物的脱卤化氢导致形成环金属化钌配合物而不是卡宾配合物。所有化合物均以溶液和固态表征。已经进行了其他密度泛函理论（DFT）研究，以阐明观察到的环金属化的机理，并阐明配体系统中不同P（V）基团对相应卡宾配合物的稳定性和反应性的影响。与PS或P N部分相比，O负责更轻松的CH活化。