[1-Hydroxy-1-phenyl-meth-(Z)-ylidene]-phosphoramidic acid diisopropyl ester | 3808-08-0

• 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: [1-Hydroxy-1-phenyl-meth-(Z)-ylidene]-phosphoramidic acid diisopropyl ester
• 英文别名: Diisopropyl benzoylamidophosphate；N-di(propan-2-yloxy)phosphorylbenzamide
• CAS: 3808-08-0
• 化学式: C₁₃H₂₀NO₄P
• 分子量: 285.28
• InChiKey: XGRJGMZUZVGTHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-Hydroxy-1-phenyl-meth-(Z)-ylidene]-phosphoramidic acid diisopropyl ester 反应 84.0h， 生成 diisopropyl N-benzoyl-N-[(chlorodimethylsilyl)methyl]phosphoramidate
  参考文献：
  名称：

  Synthesis and structure of silicon-containing N-methyland N-benzoylamides of diisopropylphosphoric acid

  摘要：

  Diisopropyl N-benzoyl-N-(trimethylsilyl)phosphoramidate reacts with ClCH2SiMe2Cl under mild conditions to form diisopropyl N-benzoyl-N-[(chlorodimethylsilyl)methyl]phosphoramidate (III). Diisopropyl N-methyl-N-(trimethylsilyl)phosphoramidate with ClCH2SiMe2Cl affords an N-transsilylation product which does not rearrange into diisopropyl N-[(chlorodimethylsilyl)methyl]-N-methylphosphoramidate (XV) even under severe conditions (4 h, 130 degrees C). Compound XV was prepared by the reaction of diisopropyl phosphorochloridate with N-[(methoxydimethylsilyl)methyl]-N-methylamine followed by treatment of diisopropyl N-[(methoxydimethylsilyl)methyl]-N-methylphosphoramidate with boron trichloride. Analysis of experimental and calculated Si-2 chemical shifts points to a five-coordinate silicon atom in compound III and a fourcoordinate silicon atom in compound XV. According to B3LYP calculations with due regard to solvent effects, compound III is an isomer with a C=O -> Si bond. By variation of substituents at silicon, phosphorus, and carbonyl carbon atoms, chelate structures with either C=O -> Si or P=O -> Si dative bonds can be obtained.

  DOI：

  10.1134/s1070363207070079
• 作为产物：
  描述：

  N-diisopropoxythiophosphorylthiobenzamide 在 水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 [1-Hydroxy-1-phenyl-meth-(Z)-ylidene]-phosphoramidic acid diisopropyl ester
  参考文献：
  名称：

  Synthesis of tetraphenylphosphonium (thio)phosphorylthiobenzamides and hydrolytic degradation to Ph3P=O, H2S and phosphoryl(thio)benzamides: A route for crystal design of PhC(X)NHP(O)(OiPr)2 (X=S, O)

  摘要：

  Reactions of the sodium salts of PhC(S)NHP(Y)(OiPr)(2) (Y=S, HLI; O, HLII) with PPh4Br in 96% aqueous EtOH leads to the corresponding compounds PPh4LIII. The structures of these compounds were investigated by IR. H-1, P-31{H-1} NMR spectroscopies; their compositions were examined by microanalysis. Recrystallization of PPh4LI,II from EtOH/H2O solution (1:1, v/v) leads to the formation of HLII and PhC(O)NHP(O)(OiPr)(2) (HLIII), respectively. The crystal structures of HLII,III are reported and compared with the previously reported polymorphs. (C) 2012 Elsevier BM. All rights reserved.

  DOI：

  10.1016/j.inoche.2012.02.041

文献信息

• Zabirov; Muratova; Kashevarov, Russian Journal of General Chemistry, 1996, vol. 66, # 3, p. 406 - 408
  作者：Zabirov、Muratova、Kashevarov、Cherkasov

  DOI：——

  日期：——
• Shokol,V.A.; Derkach,G.I., Journal of general chemistry of the USSR, 1965, vol. 35, p. 1469 - 1471
  作者：Shokol,V.A.、Derkach,G.I.

  DOI：——

  日期：——
• Zabirov, N. G.; Shamsevaleev, F. M.; Shcherbakova, V. A., Journal of general chemistry of the USSR, 1990, vol. 60, # 9.1., p. 1783 - 1789
  作者：Zabirov, N. G.、Shamsevaleev, F. M.、Shcherbakova, V. A.、Cherkasov, R. A.、Solov'ev, V. N.、et al.

  DOI：——

  日期：——
• Zabirov, N. G.; Shamsevaleev, F. M.; Cherkasov, R. A., Journal of general chemistry of the USSR, 1990, vol. 60, # 3, p. 464 - 467
  作者：Zabirov, N. G.、Shamsevaleev, F. M.、Cherkasov, R. A.

  DOI：——

  日期：——
• Zabirov, N. G.; Shamsevaleev, F. M.; Cherkasov, R. A., Journal of general chemistry of the USSR, 1992, vol. 62, # 5.1, p. 876 - 881
  作者：Zabirov, N. G.、Shamsevaleev, F. M.、Cherkasov, R. A.

  DOI：——

  日期：——