diphenyl phosphorobromidate | 70677-19-9

• 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: diphenyl phosphorobromidate
• 英文别名: diphenyl bromophosphate；bromophosphoric acid diphenyl ester；Bromophosphorsaeure-diphenylester；O,O-Diphenylphosphorylbromid；[Bromo(phenoxy)phosphoryl]oxybenzene
• CAS: 70677-19-9
• 化学式: C₁₂H₁₀BrO₃P
• 分子量: 313.087
• InChiKey: ONVDWPOQKDMJBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diphenyl phosphorobromidate 在 吡啶 、 sodium hydroxide 、 苯 作用下， 生成 phosphoric acid-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester]-diphenyl ester
  参考文献：
  名称：

  Chabrier; Carayon-Gentil, Bulletin de la Societe Chimique de France, 1957, p. 639,642

  摘要：

  DOI：
• 作为产物：
  描述：

  亚磷酸二苯酯 在 溴 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 diphenyl phosphorobromidate
  参考文献：
  名称：

  Aryl H-phosphonates. 7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates

  摘要：

  The reactions of H-phosphonate diesters with trityl and benzyl halides were investigated using P-31 NMR spectroscopy. It was found that extensive oxidation, which usually accompanies the formation of trityl- or p-nitrobenzylphosphonates from the corresponding alkyl bromides in the Michaelis-Becker reaction, can be considerably suppressed or completely eliminated by reacting p-nitrobenzyl or trityl bromides with diphenyl H-phosphonate in acetonitrile in the presence of DBU. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00790-4

文献信息

• Reinvestigation of the 31P NMR evidence for the formation of diorganyl phosphoropyridinium intermediates
  作者：Johan Nilsson、Adam Kraszewski、Jacek Stawinski

  DOI：10.1039/b107792a

  日期：2001.11.29

  A 31P NMR study on the reactions of diphenyl and diethyl chlorophosphates/bromophosphates with pyridine showed that equilibria of these reactions are heavily shifted to the left and thus concentrations of the putative diorganyl phosphoropyridinium chlorides/bromides are usually below the detection level of this spectroscopic method. However, when diphenyl iodophosphate was subjected to reaction with pyridine, we were able for the first time to observe the formation of a diorganyl phosphoropyridinium intermediate by 31P NMR spectroscopy.

  对二苯基和二乙基氯磷酸酯/溴磷酸酯与吡啶反应的31P核磁共振研究显示，这些反应的平衡强烈偏向左侧，因此理论上产生的二有机基磷吡啶盐氯化物/溴化物的浓度通常低于该光谱学方法的检测水平。然而，当二苯基碘磷酸酯与吡啶反应时，我们首次能够通过31P核磁共振光谱观察到二有机基磷吡啶盐中间体的形成。
• The reaction of diphenyl and dialkyl phosphorochloridates with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Formation of phosphonate diesters via N→C phosphorus migration
  作者：Annika Kers、Inger Kers、Jacek Stawinski

  DOI：10.1039/a904502c

  日期：——

  Diphenyl and neopentylene phosphorochloridates react with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in acetonitrile to form amidine adducts 3 or 10. These undergo further conversion into the corresponding alkene aminals, followed by probable N→C phosphorus migration to produce stable 6-substituted phosphinoyl derivatives of DBU, 6 or 12, respectively. Diethyl phosphorohalidates (chloride and bromide) also form amidine adduct 13 with DBU, but this does not undergo N→C phosphorus migration.

  二苯基和新戊二烯磷酰氯与 1,8-二氮杂双环[5.4.0]十一-7-烯（DBU）在乙腈中反应生成脒加合物 3 或 10。这些加合物进一步转化为相应的烯氨基，然后可能发生 NâC 磷迁移，分别生成稳定的 DBU、6 或 12 的 6-取代膦酰基衍生物。磷酰卤酸二乙酯（氯化物和溴化物）也会与 DBU 形成脒加合物 13，但不会发生 NâC 磷迁移。
• Kamai; Charrasowa, Metodiceskij sbornik, 1957, # 23, p. 127,130
  作者：Kamai、Charrasowa

  DOI：——

  日期：——
• A Cautionary Note on the Use of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in Conjunction with Chlorophosphates.
  作者：Annika Kers、Inger Kers、Martin Bollmark、Jacek Stawinski

  DOI：10.3891/acta.chem.scand.52-1405

  日期：——
• Kamai; Charrasowa, Metodiceskij sbornik, 1957, # 23, p. 127,131
  作者：Kamai、Charrasowa

  DOI：——

  日期：——