diethyl ester of 1-methyl-1-N-(n-butylamino)ethanephosphonic acid | 42275-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl ester of 1-methyl-1-N-(n-butylamino)ethanephosphonic acid
• 英文别名: diethyl 1-butylamino-1-methylethylphosphonate；(1-butylamino-1-methyl-ethyl)-phosphonic acid diethyl ester；N-(2-diethoxyphosphorylpropan-2-yl)butan-1-amine
• CAS: 42275-20-7
• 化学式: C₁₁H₂₆NO₃P
• 分子量: 251.306
• InChiKey: YCPTXSMGOZRACH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl ester of 1-methyl-1-N-(n-butylamino)ethanephosphonic acid 、 异氰酸甲酯 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-butyl-2-ethoxy-1,3,3-trimethyl-2-oxo-2λ5-[1,4,2]diazaphospholidin-5-one
  参考文献：
  名称：

  Merten,R.; Weber,C., Chemische Berichte, 1969, vol. 102, # 6, p. 2143 - 2145

  摘要：

  DOI：
• 作为产物：
  描述：

  N-isopropylidene-n-butylamine 、 亚磷酸二乙酯 以78%的产率得到diethyl ester of 1-methyl-1-N-(n-butylamino)ethanephosphonic acid
  参考文献：
  名称：

  SYNTHESIS AND PHYSIOLOGICAL ACTIVITIES OF NEW ACYCLIC AMINOPHOSPHONATES

  摘要：

  The dependence of biological activity of 37 newly synthesized acyclic aminomethanephosphonic acid derivatives on their structure was studied. It was found that the phytotoxicity of the compounds studied depended on their hydrophobic parameters, and in a smaller extent on the electronic parameters of the substituents on nitrogen and phosphorus atoms. No phytotoxicity dependence on the steric parameters of compounds was found. Tested organism was Spirodela oligorrhiza and the parameter studied was the concentration of compounds causing 50 % growth inhibition (EC50) The test had preliminary character and permitted to eliminate the less promising compounds out of further studies.

  DOI：

  10.1080/10426500008076535

文献信息

• Nucleophilic addition to carbonyl compounds. competition between hard (amine) and soft (phosphite) nucleophile
  作者：Roman Gancarz

  DOI：10.1016/0040-4020(95)00634-k

  日期：1995.9

  reaction mixture, two nucleophiles: dialkyl phosphite and the amine compete for the electrophilic carbonyl compound. Reaction mixture composition studies, kinetic studies as well as theoretical calculations, indicate that the softer the carbonyl compound is, the faster it reacts with the softer phosphorus nucleophile and the slower it reacts with the harder amine nucleophile. It in turn results in

  在Kabachnik Fields反应混合物中，两个亲核试剂：亚磷酸二烷基酯和胺竞争亲电羰基化合物。反应混合物组成研究，动力学研究以及理论计算表明，羰基化合物越软，与较软的磷亲核试剂反应越快，而与较硬的胺亲核试剂反应越慢。反过来导致产物的比例不同，即形成氨基膦酸酯与羟基膦酸酯。
• Ivanova,Zh.M. et al., Journal of general chemistry of the USSR, 1976, vol. 46, # 2, p. 233 - 238
  作者：Ivanova,Zh.M. et al.

  DOI：——

  日期：——
• Gancarz, Roman; Gancarz, Irena; Walkowiak, Urszula, Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 104, # 14, p. 45 - 52
  作者：Gancarz, Roman、Gancarz, Irena、Walkowiak, Urszula

  DOI：——

  日期：——
• Failure of aminophosphonate synthesis due to facile hydroxyphosphonate - phosphate rearrangement
  作者：Roman Gancarz、Irena Gancarz

  DOI：10.1016/s0040-4039(00)60079-5

  日期：1993.1

  In a Kabachnik-Fields synthesis of aminophosphonates amines can catalyse the formation of hydroxyphosphonates, and their further rearrangement to phosphates, unabling the formation of aminophosphonates.