Diphenylphosphoryl methyl carbonate | 170303-71-6

• 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: Diphenylphosphoryl methyl carbonate
• CAS: 170303-71-6
• 化学式: C₁₄H₁₃O₄P
• 分子量: 276.229
• InChiKey: MRDXVXALHCBIAS-UHFFFAOYSA-N

物化性质

• 沸点：
  377.9±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diphenylphosphoryl methyl carbonate 以 四氢呋喃 为溶剂， 生成 [甲氧基(苯基)磷酰基]苯
  参考文献：
  名称：

  Mixed Anhydrides: Key Intermediates in Carbamates Forming Processes of Industrial Interest

  摘要：

  Mixed anhydrides of carbonic acid with phosphonic or carbamic acid, are mimic of relevant biological systems, and behave as key intermediates in trans-esterification processes that afford carbamates of industrial interest. They are formed in the phosphonic acids mediated or direct transesterification reaction of organic carbonates with amines to afford carbamates and have been isolated and characterised in the solid state and solution. Their conversion into the products has been demonstrated to occur with high regioselectivity. The application of such intermediates in some synthetic processes is discussed.

  DOI：

  10.1002/1521-3765(20020201)8:3<685::aid-chem685>3.0.co;2-1
• 作为产物：
  描述：

  sodium methyl carbonate 、 二苯基次膦酰氯 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到Diphenylphosphoryl methyl carbonate
  参考文献：
  名称：

  氨基甲酸酯部分的仿生堆积：羧基磷酸酯类似物在由磷酸促进的芳基胺和有机碳酸酯合成N-芳基氨基甲酸酯的过程中的中介作用

  摘要：

  在有机磷酸[Ph 2 P（O）OH（1）;的存在下，芳族胺与碳酸二甲酯（DMC）或碳酸二苯酯（DPC）的反应。（PhO）2 P（O）OH（2）; （BuO）2 P（O）OH /（BuO）P（O）（OH）2等摩尔混合物（3）]产生具有高选择性的氨基甲酸酯ArNHC（O）OR（R = Me，Ph）。对P-酸所起的催化作用已进行了研究，并根据涉及中间形成碳-次膦酸（磷）酸酐X 2的反应机理进行了合理化研究。P（O）OC（O）OR（X = Ph，PhO; R = Me，Ph）。所提出的机制与通过氨基甲酰磷酸合成酶（CPS）酶在生物系统中形成氨基甲酸酯阴离子的机制具有相似的趣味。

  DOI：

  10.1016/0040-4020(95)00424-7

文献信息

• Mixed Anhydrides: Key Intermediates in Carbamates Forming Processes of Industrial Interest
  作者：Michele Aresta、Angela Dibenedetto

  DOI：10.1002/1521-3765(20020201)8:3<685::aid-chem685>3.0.co;2-1

  日期：2002.2.1

  Mixed anhydrides of carbonic acid with phosphonic or carbamic acid, are mimic of relevant biological systems, and behave as key intermediates in trans-esterification processes that afford carbamates of industrial interest. They are formed in the phosphonic acids mediated or direct transesterification reaction of organic carbonates with amines to afford carbamates and have been isolated and characterised in the solid state and solution. Their conversion into the products has been demonstrated to occur with high regioselectivity. The application of such intermediates in some synthetic processes is discussed.
• Biomimetic building-up of the carbamic moiety: the intermediacy of carboxyphosphate analogues in the synthesis of N-aryl carbamate esters from arylamines and organic carbonates promoted by phosphorus acids
  作者：Michele Aresta、Chlara Berloco、Eugenio Quaranta

  DOI：10.1016/0040-4020(95)00424-7

  日期：1995.7

  The reaction of aromatic amines with dimethyl carbonate (DMC) or diphenyl carbonate (DPC) in the presence of organo-phosphorus acids [Ph2P(O)OH (1); (PhO)2P(O)OH (2); (BuO)2P(O)OH/(BuO)P(O)(OH)2 equimolar mixture (3)] affords carbamate esters, ArNHC(O)OR (R = Me, Ph) with high selectivity. The catalytic role played by the P-acid has been investigated and rationalized in terms of a reaction mechanism

  在有机磷酸[Ph 2 P（O）OH（1）;的存在下，芳族胺与碳酸二甲酯（DMC）或碳酸二苯酯（DPC）的反应。（PhO）2 P（O）OH（2）; （BuO）2 P（O）OH /（BuO）P（O）（OH）2等摩尔混合物（3）]产生具有高选择性的氨基甲酸酯ArNHC（O）OR（R = Me，Ph）。对P-酸所起的催化作用已进行了研究，并根据涉及中间形成碳-次膦酸（磷）酸酐X 2的反应机理进行了合理化研究。P（O）OC（O）OR（X = Ph，PhO; R = Me，Ph）。所提出的机制与通过氨基甲酰磷酸合成酶（CPS）酶在生物系统中形成氨基甲酸酯阴离子的机制具有相似的趣味。