α-((bis(phenyloxy)phosphoryl)oxy)acetophenone | 16222-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-((bis(phenyloxy)phosphoryl)oxy)acetophenone
• 英文别名: α-(diphenyloxyphosphoryloxy)acetophenone；α-(diphenylphosphoryloxy)acetophenone；PhCOCH2OPO(OPh)2；Orthophosphorsaeure-diphenyl-phenacyl-ester；Phenacyl diphenyl phosphate
• CAS: 16222-22-3
• 化学式: C₂₀H₁₇O₅P
• 分子量: 368.326
• InChiKey: PIUGLSVCGOAZFV-UHFFFAOYSA-N

物化性质

• 沸点：
  476.0±37.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  磷酸二苯酯 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 α-((bis(phenyloxy)phosphoryl)oxy)acetophenone
  参考文献：
  名称：

  新型[羟基（甲苯磺酰氧基）碘]芳烃和[羟基（磷酸酰氧基）碘]芳烃对酮的α-甲苯磺酰化和α-磷酸酰氧基化的反应性。

  摘要：

  具有2-噻吩基，3-噻吩基，N-甲苯磺酰基-4-吡唑基，3-三氟甲基苯基和3,5-双（三氟甲基）苯基作为芳族基团和[羟基（磷酰氧基）的新型[羟基（甲苯磺酰氧基）碘]芳烃制备了带有N-甲苯磺酰基-4-吡唑基，3-三氟甲基苯基和3,5-双（三氟甲基）苯基作为芳香族基团的碘代芳烃。用这些化合物分别进行酮的α-甲苯磺酰化和α-磷酸酰化。将它们的反应性分别与母体[羟基（甲苯磺酰氧基）碘]苯和[羟基（磷酸甲酰氧基）碘]苯进行比较，因此将[羟基（甲苯磺酰氧基）碘]芳烃和[3]作为芳族基团的-三氟甲基苯基和3,5-双（三氟甲基）苯基显示出最佳的反应性。

  DOI：

  10.1021/jo0200670

文献信息

• An Efficient Microwave-Promoted Solvent-Free α-Phosphoryloxylation of Ketones
  作者：Ye Pu、Yingguo Fang、Jie Yan

  DOI：10.2174/157017812802139717

  日期：2012.7.1

  An efficient solvent-free α-phosphoryloxylation of ketones under microwave irradiation is reported. When ketones reacted with phosphates and (diacetoxyiodo)benzene under microwave irradiation for short time, the α-phosphoryloxylaction of ketones was easily be carried out and the corresponding ketol phosphates were prepared in moderate to good yields.

  据报道，酮在微波辐射下进行了有效的无溶剂 α-磷酰氧基化。当酮 磷酸酯与(二乙酰氧基碘)苯在微波照射下短时间反应，很容易发生酮的α-磷酰氧基化反应，在适度的反应条件下制备了相应的酮醇磷酸酯。 以获得良好的产量。
• An Effective Catalytic α-Phosphoryloxylation of Ketones with Iodobenzene
  作者：Jie Yan、Ye Pu、Liumian Gao、Huijun Liu

  DOI：10.1055/s-0031-1289630

  日期：2012.1

  An effective catalytic method for α-phosphoryloxylation of ketones is reported. When ketones were reacted with phosphates in the presence of iodobenzene as the recyclable catalyst and m-chloroperbenzoic acid as the terminal oxidant in acetonitrile at room temperature, the α-phosphoryloxylation of ketones took place easily and the corresponding keto phosphates were obtained in moderate to good yields.

  报告了一种有效的催化方法，用于酮的δ-磷酰氧基化反应。在室温下，以碘苯为可回收催化剂，间氯过苯甲酸为末端氧化剂，在乙腈中使酮与磷酸盐反应，酮的δ-磷酰氧基化反应很容易发生，并以中等至良好的收率获得相应的酮磷酸盐。
• O–H Insertion of Hydrogenphosphate Derivatives and α-Diazo Compounds
  作者：Fei Tan、Wei Wang、Xiao Huang、Yi Zhong、Tao Song、Jian Wang、Ling Mei

  DOI：10.1021/acs.joc.3c02605

  日期：2024.2.16

  An efficient O–H insertion of hydrogenphosphate derivatives and α-diazo compounds has been developed to construct α-phosphoryloxy scaffolds. Diverse α-phosphoryloxy skeletons could be obtained under mild and catalyst-free conditions in good yields. The control experiments suggest a protonation and nucleophilic addition process of α-diazo compounds via a diazonium ion pair for this transformation.

  磷酸氢盐衍生物和 α-重氮化合物的有效 ​​O-H 插入已被开发用于构建 α-磷酰氧基支架。在温和且无催化剂的条件下可以以良好的产率获得多种α-磷酰氧基骨架。对照实验表明，α-重氮化合物通过重氮离子对进行质子化和亲核加成过程，以实现该转化。
• Novel Oxidative α-Tosyloxylation of Alcohols with Iodosylbenzene and <i>p</i>-Toluenesulfonic Acid and Its Synthetic Use for Direct Preparation of Heteroaromatics
  作者：Makoto Ueno、Takahiro Nabana、Hideo Togo

  DOI：10.1021/jo030045t

  日期：2003.8.1

  alpha-Tosyloxyketones and alpha-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidazo[1,2-alpha]pyridines from alcohols in good to moderate yields by the successive treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate, followed by thioamides, benzamidine, and 2-aminopyridine, respectively.
• Direct .alpha.-phosphoryloxylation of ketones and (phosphoryloxy)lactonization of pentenoic acids with [hydroxy[(bis(phenyloxy)phosphoryl)oxy]iodo]benzene
  作者：Gerald F. Koser、Jayant S. Lodaya、Dale G. Ray、Pandurang B. Kokil

  DOI：10.1021/ja00217a058

  日期：1988.4