α-(diphenylphosphoryloxy)propiophenone | 440365-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(diphenylphosphoryloxy)propiophenone
• 英文别名: Phosphoric acid, 1-methyl-2-oxo-2-phenylethyl diphenyl ester；(1-oxo-1-phenylpropan-2-yl) diphenyl phosphate
• CAS: 440365-93-5
• 化学式: C₂₁H₁₉O₅P
• 分子量: 382.353
• InChiKey: DCPXHFCXCQQLTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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 、 1-苯丙醇 在 亚碘酰苯 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以62%的产率得到α-(diphenylphosphoryloxy)propiophenone
  参考文献：
  名称：

  Novel Oxidative α-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid and Its Synthetic Use for Direct Preparation of Heteroaromatics

  摘要：

  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.

  DOI：

  10.1021/jo030045t

文献信息

• Reactivities of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for α-Tosyloxylation and α-Phosphoryloxylation of Ketones
  作者：Takahiro Nabana、Hideo Togo

  DOI：10.1021/jo0200670

  日期：2002.6.1

  [hydroxy(tosyloxy)iodo]arenes bearing 2-thienyl, 3-thienyl, N-tosyl-4-pyrazolyl, 3-trifluoromethylphenyl, and 3,5-bis(trifluoromethy)phenyl as an aromatic group, and [hydroxy(phosphoryloxy)iodo]arenes bearing N-tosyl-4-pyrazolyl, 3-trifluoromethylphenyl, and 3,5-bis(trifluoromethy)phenyl as an aromatic group, were prepared. alpha-Tosyloxylation and alpha-phosphoryloxylation of ketones with these compounds were

  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。
• 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。
• 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.