phosphoric acid ethyl ester-anilide chloride | 155051-55-1

• 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: phosphoric acid ethyl ester-anilide chloride
• 英文别名: Anilin-N-phosphinsaeure-aethylester-chlorid；Phosphorsaeure-aethylester-anilid-chlorid；O-ethyl-N-phenyl amidochlorophosphate；N-[chloro(ethoxy)phosphoryl]aniline
• CAS: 155051-55-1
• 化学式: C₈H₁₁ClNO₂P
• 分子量: 219.608
• InChiKey: CPOGNDBVMHSMMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.3±23.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phosphoric acid ethyl ester-anilide chloride 在 乙醚 、 氨 作用下， 生成 phenyl-diamidophosphoric acid ethyl ester
  参考文献：
  名称：

  Caven, Journal of the Chemical Society, 1902, vol. 81, p. 1367

  摘要：

  DOI：
• 作为产物：
  描述：

  二氯磷酸乙酯 、 苯胺 在 乙醚 作用下， 生成 phosphoric acid ethyl ester-anilide chloride
  参考文献：
  名称：

  Caven, Journal of the Chemical Society, 1902, vol. 81, p. 1367

  摘要：

  DOI：

文献信息

• Antibacterial Organophosphorus Compounds: Phosphoranilidohydrazones of 5-Nitro-2-furaldehyde
  作者：Gerald S. Jones、Jennifer S. Daly

  DOI：10.1002/jps.2600820716

  日期：1993.7

  series of phosphoranilidohydrazones of 5-nitro-2-furaldehyde was synthesized and evaluated for antibacterial activity. The series was prepared to examine the applicability of phosphoramidic hydrazones as carriers for the antibacterial nitrofuran moiety. Designed as analogues of nitrofurantoin, members of the series were chosen according to the Topliss approach to analogue design. The title compounds were

  合成了一系列5-硝基-2-呋喃甲醛的磷酰氨基hydr，并对其抗菌活性进行了评估。制备该系列以检查磷酰胺作为抗菌剂硝基呋喃部分的载体的适用性。被设计为硝基呋喃妥因的类似物，根据Topliss的类似物设计方法选择了该系列的成员。标题化合物没有革兰氏阴性活性，但具有中等的抗葡萄球菌活性。该系列中最有效的成员是与呋喃妥因对金黄色葡萄球菌等效的。讨论了结构与抗葡萄球菌活性之间的关系。
• Phosphorylation with monomeric metaphosphates
  申请人：Research Corporation Technologies, Inc.

  公开号：US05334741A1

  公开（公告）日：1994-08-02

  Solid substrates with free hydroxyl groups are phosphorylated by thermolysing a solution of phosphoramidate of the formula ##STR1## in the presence of the substrate, whereby metaphosphate is generated which phosphorylates the substrate.

  具有自由羟基固体基质在存在基质的情况下，通过热解式磷酰胺盐溶液（式子如下）的磷酸化作用，生成亚磷酸酯，从而磷酸化基质。
• Rastogi, R. C.; Khan, R. H.; Baruah, K. R., Journal of the Indian Chemical Society, 1992, vol. 69, # 3, p. 161 - 162
  作者：Rastogi, R. C.、Khan, R. H.、Baruah, K. R.

  DOI：——

  日期：——
• SYNTHESIS AND QUANTITATIVE OF STRUCTURE-ACTIVITY RELATIONSHIPS OF PHOSPHORAMIDATES AND PHOSPHORODIAMIDATES INCORPORATING AMINO ACID ESTERS
  作者：Hussein M. Ali、Zidan H. Zidan

  DOI：10.1080/10426500008046609

  日期：2000.8.1

  Two series of O-aryl and N-aryl O-ethyl phosphoramidates and phosphorodiamidates respectively containing alpha -amino acid ester moieties have been synthesized and characterized by H-1 NMR, IR and mass spectroscopy. Stepwise multiple regression analysis showed that the anticholinesterase activity was strongly correlated with the chemical structures represented by the stereo-electronic and hydrophobic parameters with correlation coefficient of 0.999. These results revealed that the inhibition activity of both series was inversely correlated with the steric bulk of the p-aryl substituents and directly with the bulk of the alkyl groups of the amino acid moieties, whereas m-aryl substituents have no steric effect on the inhibition process. The inhibition was enhanced by strong pi -electron acceptor aryl substituents and reduced by electron donating alkyl groups of the amino acids. This supported the proposed inhibition mechanism of nucleophilic attack of a hydroxyl group at the enzyme active site on the partially positive phosphorus atom in organophosphorus compounds. The inhibition was also increased by more hydrophilic substituents. These results showed the importance of both the reactivity of these compounds and their steric interaction with the AChE active site in controlling enzyme inhibition, in addition to the ease of more hydrophobic compounds to reach the enzyme active site.
• O-Ethyl Phosphoramidic Acids with Sterically Demanding N-Substituents: Useful Precursors of Ethyl Metaphosphate on Thermolysis
  作者：Louis D. Quin、Stefan Jankowski

  DOI：10.1021/jo00095a013

  日期：1994.8

  Kinetics of the thermal fragmentation of four N-substituted derivatives of O-ethyl phosphoramidic acids, (EtO-P(O)(NRR')(OH), were examined. When N contained either of the sterically demanding mesityl or 1-adamantyl groups, the reaction followed first-order kinetics, both in the absence and presence of an alcohol trapping reagent. In the former case, the product was a pyrophosphate (RR'N(EtO)(O)P-O-P(O)(OEt)OH). In the latter case, phosphorus was trapped as a dialkyl phosphate. Both reactions are therefore indicated to follow an elimination-addition mechanism, with ethyl metaphosphate as transient intermediate. The pyrophosphate is derived from reaction of the metaphosphate with unreacted phosphoramidic acid. With less bulky substituents (N-phenyl or N,N-diethyl), mixed first- and second-order kinetics were followed in the absence of a trapping agent; some bimolecular interaction of the substrate to form the pyrophosphate product is indicated by the second-order kinetics. Product analyses and quantitative measurements were made with P-31 NMR spectroscopy. From all phosphoramidic acids, the intermediate metaphosphate was effectively trapped by reaction with the OH group on the surface of solid silica gel. The presence of covalently bonded phosphate on the surface was shown by P-31 and Si-29 CP/MAS NMR spectroscopy.