1-(diphenylphosphoryl)-1-phenylethanol | 33455-12-8

• 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: 1-(diphenylphosphoryl)-1-phenylethanol
• 英文别名: (1-hydroxy-1-phenylethyl)diphenylphosphine oxide；1-Hydroxy-1-phenylethyl(diphenyl)phosphinoxid；1-Diphenylphosphoryl-1-phenylethanol
• CAS: 33455-12-8
• 化学式: C₂₀H₁₉O₂P
• 分子量: 322.343
• InChiKey: YPAJQDCAAMEVKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯乙酮 、 Diphenylphosphine oxide 以99 %的产率得到1-(diphenylphosphoryl)-1-phenylethanol
  参考文献：
  名称：

  醛的三组分直接磷酸化和酮的烷基化：酸性条件下γ-酮氧化膦的合成

  摘要：

  开发了一种有效且经济的酸促进三组分反应，用于构建 C-P 和 C-C 键，用于合成 γ-酮膦氧化物，水作为唯一的副产物。详细的机理实验证实，该反应通过磷醛醇消除进行，其中醛的磷酸化产生苄基碳正离子，然后在酸性条件下与酮烯醇化物反应。

  DOI：

  10.1021/acs.joc.3c01674

文献信息

• Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides
  作者：Boris A. Trofimov、Nina K. Gusarova、Nina I. Ivanova、Kseniya O. Khrapova、Pavel A. Volkov、Anton A. Telezhkin、Lyudmila I. Larina、Andrei V. Afonin、Dmitry V. Pavlov

  DOI：10.1055/s-0040-1707945

  日期：2020.8

  α-hydroxyphosphine oxides have been synthesized via the catalyst- and solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20–62 °C in near to 96–98% yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level

  叔α-羟基膦氧化物是在20-62°C下通过可用的仲膦氧化物与脂肪族，芳香族和杂芳香族酮之间的无催化剂和无溶剂反应合成的，产率接近96-98％。所开发的方法符合绿色化学和PASE（锅，原子，阶梯经济）范式的要求。根据在B3LYP / 6-311 ++ G（d，p）水平上的量子化学计算，合成的羟基膦氧化物具有弱的（≈3kcal·mol –1）OH···O = P分子内氢键。
• The Reaction Activity of Aromatic Carbonyl Compounds with Diphenylphosphine Oxide Studied by ³¹P NMR
  作者：Jinyun Zheng、Xiangming Feng、Yujian Yu、Xiaomin Zhen、Yufen Zhao

  DOI：10.1080/10426507.2012.717137

  日期：2013.8.1

  A series of -hydroxyphosphine oxides were prepared by the reactions of diphenylphosphine oxide and aromatic carbonyl compounds and characterized by H-1 NMR, C-13 NMR, P-31 NMR, FT-IR, ESI-MS, and HR-MS spectra. The reaction rates and experimental conditions of aromatic aldehydes and aromatic ketones were obviously different due to the activity of their carbonyls. The different substituents of the aromatic aldehydes affected the reaction rate too, and the quantitative reactivity of their substituent conformed to the Hammett equation. The results were confirmed by P-31 NMR spectroscopy.