(2-Oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester | 681035-22-3

• 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: (2-Oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester
• 英文别名: 3-Diphenoxyphosphoryl-5,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 681035-22-3
• 化学式: C₂₇H₂₂NO₅P
• 分子量: 471.449
• InChiKey: BOTIKSVXRZWKMI-UHFFFAOYSA-N

物化性质

• 沸点：
  577.2±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  鸟苷 、 (2-Oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester 在 N,N-双(苯基亚甲基)-1,2-乙二胺 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 、 水 、 silica gel 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 48.0h， 以54%的产率得到Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester phenyl ester
  参考文献：
  名称：

  Phosphorylation of Alcohols with N-Phosphoryl Oxazolidinones Employing Copper(II) Triflate Catalysis

  摘要：

  Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.

  DOI：

  10.1021/ol051104n
• 作为产物：
  描述：

  tert-butyl (2-hydroxy-2,2-diphenylethyl)carbamate 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (2-Oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester
  参考文献：
  名称：

  N-Phosphoryl oxazolidinones as effective phosphorylating agents

  摘要：

  A number of N-phosphoryl oxazolidinones have been prepared and evaluated, the best being 5,5-diphenyl oxazolidinones, the utility of which was demonstrated in the phosphorylation of a number of representative primary, secondary, tertiary, and phenolic alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.003

文献信息

• N-Phosphoryl oxazolidinones as effective phosphorylating agents
  作者：Simon Jones、Chaiwat Smanmoo

  DOI：10.1016/j.tetlet.2004.01.003

  日期：2004.2

  A number of N-phosphoryl oxazolidinones have been prepared and evaluated, the best being 5,5-diphenyl oxazolidinones, the utility of which was demonstrated in the phosphorylation of a number of representative primary, secondary, tertiary, and phenolic alcohols. (C) 2004 Elsevier Ltd. All rights reserved.
• Phosphorylation of Alcohols with <i>N</i>-Phosphoryl Oxazolidinones Employing Copper(II) Triflate Catalysis
  作者：Simon Jones、Chaiwat Smanmoo

  DOI：10.1021/ol051104n

  日期：2005.7.1

  Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.