Diethyl N-benzylthiophosphoramidate | 55739-98-5

• 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: Diethyl N-benzylthiophosphoramidate
• 英文别名: N-diethoxyphosphinothioyl-1-phenylmethanamine
• CAS: 55739-98-5
• 化学式: C₁₁H₁₈NO₂PS
• 分子量: 259.309
• InChiKey: NBYDMVDXNLJGNU-UHFFFAOYSA-N

物化性质

• 沸点：
  331.3±35.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethyl N-benzylthiophosphoramidate 在 sodium hydroxide 、 双氧水 、 sodium hydride 、 9-硼双环[3.3.1]壬烷 作用下， 反应 6.0h， 生成 diethylthiophosphoramidate de N-benzyle et de N-(hydroxy-3 propyle)
  参考文献：
  名称：

  Benmaarouf-Khallaayoun, Z.; Baboulene, M.; Speziale, V., Synthetic Communications, 1985, vol. 15, # 3, p. 233 - 242

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(O,O-diethyl)thiophosphoryl phenylimine 在 diethylzinc 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到Diethyl N-benzylthiophosphoramidate
  参考文献：
  名称：

  Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

  摘要：

  This report describes the reaction of N-(thio)phosphoryl imines with diethylzine under different conditions. An interesting and distinct chemoselectivity between hydrogen-addition and ethyl-addition to imine double bond is disclosed: in weakly polar solvent, e.g. toluene, N-(thio)phosphoryl imines were exclusively reduced in excellent yields via a beta-H transfer from diethylzinc to imine double bond; in polar solvents like THF, the reduction product was competitively formed as a major product together with the minor product resulting from ethyl-addition to imine double bond; in sharp contrast, in the presence of strong coordinative additive N,N,N',N'-tetramethylethylenediamine (TMEDA), the ethylation product was formed exclusively from the reaction of N-(thio)phosphoryl imine with diethylzinc. These results are discussed and explained in terms of the coordination interactions between the imine, solvent, and additive with diethylzinc. (c) 2007 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.05.001

文献信息

• Catalytic enantioselective alkylation of aldehydes using chiral hydrogen phosphoramidates and hydrogen phosphinamides and their thio analogs
  作者：Kenso Soai、Yoshiaki Ohno、Yukikazu Inoue、Toshihiro Tsuruoka、Yuji Hirose

  DOI：10.1002/recl.19951140404

  日期：——

  Chiral (enantiomerically pure) hydrogen thiophosphoramidates and hydrogen phosphoramidates and their phosphinamide analogs derived from norephedrine and other chiral (enantiomerically pure) amino alcohols catalyze the enantioselective addition of dialkylzines to aldehydes. The presence of titanium tetraisopropoxide increases the enantioselectivity, providing enantiomerically enriched secondary alcohols

  衍生自去甲麻黄碱和其他手性（对映体纯的）氨基醇的手性（对映体纯的）硫代磷酰胺酸氢盐和氨基磷酸氢盐及其次膦酰胺类似物催化二烷基嗪与醛的对映选择性加成。四异丙氧基钛的存在增加了对映选择性，为对映体富集的仲醇提供了高达98％的ee。硫代磷酰胺化物和硫代膦酰胺的对映选择性高于氧类似物的对映选择性。在没有Ti（O i Pr）4的情况下，没有羟基的氨基磷酸酯和硫代磷酰胺酸酯也催化将二烷基锌加成到醛上。
• Methanolysis of phosphoramidates with boron trifluoride-methanol complex
  作者：Seungmin Ryu、John A. Jackson、Charles M. Thompson

  DOI：10.1021/jo00016a042

  日期：1991.8
• BENMAAROUF-KHALLAAYOUN, Z.;BABOULENE, M.;SPEZIALE, V.;LATTES, A., SYNTH. COMMUN., 1985, 15, N 3, 233-241
  作者：BENMAAROUF-KHALLAAYOUN, Z.、BABOULENE, M.、SPEZIALE, V.、LATTES, A.

  DOI：——

  日期：——