α-(ethyloxycarbonylamino)benzyl-2-(ethyloxycarbonyl)ethylphosphinic acid | 1029774-18-2

• 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: α-(ethyloxycarbonylamino)benzyl-2-(ethyloxycarbonyl)ethylphosphinic acid
• 英文别名: α-(ethoxycarbonylamino)-benzyl-2-(ethoxycarbonyl)-ethylphosphonic acid；α-(ethoxycarbonylamino)benzyl[2-(ethoxycarbonyl)ethyl]phosphinic acid；[(Ethoxycarbonylamino)-phenylmethyl]-(3-ethoxy-3-oxopropyl)phosphinic acid；[(ethoxycarbonylamino)-phenylmethyl]-(3-ethoxy-3-oxopropyl)phosphinic acid
• CAS: 1029774-18-2
• 化学式: C₁₅H₂₂NO₆P
• 分子量: 343.317
• InChiKey: BGYNYULTMKVELZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲醛 在 乙酸酐 、 三氟乙酸酐 作用下， 生成 α-(ethyloxycarbonylamino)benzyl-2-(ethyloxycarbonyl)ethylphosphinic acid
  参考文献：
  名称：

  Acyloxy derivatives of trivalent phosphorus in amidoalkylation of hydrophosphoryl compounds

  摘要：

  In order to model the previously suggested mechanism of the P-C bond formation via the Arbuzov reaction, we have studied the interaction of diethylacylphosphite (prepared beforehand as well as generated in situ from tetraethylpyrophosphite) with the in situ generated acyliminium cation. Various conditions of in situ generation of acylphosphite derivatives of P(III) from hydrophosphoryl compounds and acyliminium ions from N,N'-alkylidenebiscarbamates have been investigated: solvent nature, acid catalyst, and the reagents mixing order). The results obtained have confirmed the suggested mechanism of three-component reaction of amidoalkylation of hydrophosphoryl compounds with the formation of P-C bond via the Arbuzov reaction of in situ formed intermediates.

  DOI：

  10.1134/s1070363213100150

文献信息

• Arbuzov-type reaction of acylphosphonites and N-alkoxycarbonylimine cations generated in situ with trifluoroacetic anhydride
  作者：Maxim E. Dmitriev、Valery V. Ragulin

  DOI：10.1016/j.tetlet.2012.01.094

  日期：2012.3

  N-protected α-aminoalkylphosphinic acids by the reaction of N,N′-benzylidene- or N,N′-alkylidenebiscarbamates, trifluoroacetic anhydride and the corresponding alkylphosphonous acids in methylene chloride or toluene is described. The results obtained confirm the earlier proposed mechanism for amidoalkylation of hydrophosphorylic compounds involving an Arbuzov-type reaction step.

  描述了通过N，N'-亚苄基-或N，N'-亚烷基双氨基甲酸酯，三氟乙酸酐和相应的烷基亚膦酸在二氯甲烷或甲苯中反应合成N-保护的α-氨基烷基次膦酸的温和方法。获得的结果证实了较早提出的涉及Arbuzov型反应步骤的氢磷酸化合物酰胺烷基化的机理。
• New opinions on the amidoalkylation of hydrophosphorylic compounds
  作者：Maxim E. Dmitriev、Valery V. Ragulin

  DOI：10.1016/j.tetlet.2010.03.020

  日期：2010.5

  A new and milder version of the procedure for the synthesis of N-protected α-aminoalkylphosphorylic compounds by reaction of alkyl carbamates, aldehydes and hydrophosphorylic compounds in acetic anhydride/acetyl chloride and a new mechanism for this type of reaction are described. The isolation, for the first time, of N,N′-benzylidene- and N,N′-alkylidenebiscarbamates as intermediates from the reaction

  描述了通过氨基甲酸烷基酯，醛和氢磷酸化合物在乙酸酐/乙酰氯中的反应合成N-保护的α-氨基烷基磷酸化合物的程序的一种新的，较温和的方法，以及这种反应的新机理。首次报道了从反应介质中分离出作为中间体的N，N′-亚苄基-和N，N′-亚烷基双氨基甲酸酯，并研究了预先获得的双氨基甲酸酯和氢磷酸化合物在乙酸酐中的直接反应。提出了该反应机理的新形式，其中包括Arbuzov型反应。
• Acyloxy derivatives of trivalent phosphorus in amidoalkylation of hydrophosphoryl compounds
  作者：M. E. Dmitriev、V. V. Ragulin

  DOI：10.1134/s1070363213100150

  日期：2013.10

  In order to model the previously suggested mechanism of the P-C bond formation via the Arbuzov reaction, we have studied the interaction of diethylacylphosphite (prepared beforehand as well as generated in situ from tetraethylpyrophosphite) with the in situ generated acyliminium cation. Various conditions of in situ generation of acylphosphite derivatives of P(III) from hydrophosphoryl compounds and acyliminium ions from N,N'-alkylidenebiscarbamates have been investigated: solvent nature, acid catalyst, and the reagents mixing order). The results obtained have confirmed the suggested mechanism of three-component reaction of amidoalkylation of hydrophosphoryl compounds with the formation of P-C bond via the Arbuzov reaction of in situ formed intermediates.