diethyl trifluoroacetimidoyl phosphonate | 956410-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl trifluoroacetimidoyl phosphonate
• 英文别名: O,O-diethyl α-iminotrifluoroethylphosphonate；1-Diethoxyphosphoryl-2,2,2-trifluoroethanimine；1-diethoxyphosphoryl-2,2,2-trifluoroethanimine
• CAS: 956410-70-1
• 化学式: C₆H₁₁F₃NO₃P
• 分子量: 233.127
• InChiKey: BHJJYAWPLHBPKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl trifluoroacetimidoyl phosphonate 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到diethyl (1-amino-2,2,2-trifluoroethyl)phosphonate
  参考文献：
  名称：

  氨基膦酸衍生物不对称合成的新策略：C-磷酸化亚胺的首次对映选择性催化还原

  摘要：

  报道了1-亚氨基-2,2,2-三氟乙基膦酸酯的首次高对映选择性催化还原和对映异构体富集的生物相关膦酰基三氟丙氨酸的合成。

  DOI：

  10.1016/j.tetlet.2008.10.152
• 作为产物：
  描述：

  diethyl [2,2,2-trifluoro-N-(trimethylsilyl)ethanimidoyl]phosphonate 在 甲醇 作用下， 以 乙醚 为溶剂， 生成 diethyl trifluoroacetimidoyl phosphonate
  参考文献：
  名称：

  甲硅烷基亚氨基膦酸酯：用于制备氟化氨基膦酸酯和氨基膦酸的新型反应性合成子

  摘要：

  已开发出一种方便的合成方法，用于处理以前未知的在亚胺C原子上带有氟代烷基的N-和N，O-甲硅烷基化的α-亚氨基膦酸酯。化合物的合成潜力很容易被其官能化，并且可以直接制备生物相关的氨基膦酸酯和带有在α位上带有杂环残基的游离氨基膦酸。

  DOI：

  10.1016/j.tetlet.2017.07.075

文献信息

• α-Iminotrifluoroethylphosphonates: The First Representatives of N-H Imidoyl Phosphonates
  作者：Petro Onys’ko、Yuliya Rassukana、Mykola Kolotylo、Oleksii Sinitsa、Volodymir Pirozhenko

  DOI：10.1055/s-2007-983838

  日期：2007.9

  A convenient synthetic approach to previously unknown N-H imidoyl phosphonates, based on addition of dialkyl phosphites to trifluoroacetonitrile, has been developed. The synthetic potential of such imines, which exist as equilibrium mixtures of E/Z-isomers, was demonstrated by their easy reduction and functionalization with O- and P-centered nucleophiles, to afford derivatives of α-aminophosphonic acids containing a trifluoromethyl group. Furthermore, interaction with mercaptoacetic acid proceeds with intramolecular cyclization of the intermediate adduct to produce a novel 2-phosphorylated N-H thiazolidone. Interaction between the N-H imines and trichloroacetylisocyanate leads to novel, reactive, phosphorylated N-acylated imines.

  我们开发了一种基于二烷基亚磷酸酯与三氟乙腈加成的，合成先前未知的N-H亚胺基膦酸酯的便捷方法。这类亚胺存在E/Z异构体平衡混合物，通过它们的易还原性和O/P中心亲核试剂的官能化，展示了其合成潜力，制备了含有三氟甲基的α-氨基膦酸衍生物。此外，与巯基乙酸的反应通过中间加成物的分子内环化，生成了一种新型2-膦酸化的N-H噻唑烷酮。N-H亚胺与三氯乙酰异氰酸酯的反应产生新型、活性高的磷酸化N-酰基亚胺。
• α—Iminotrifluoroethyl Phosphonates: The First Representatives of C-Phosphorylated N-H Imines
  作者：A. D. Sinitsa、M. V. Kolotylo、Yu. V. Rassukana、V. V. Pirozhenko、P. P. Onys'ko

  DOI：10.1080/10426500701793287

  日期：2008.1.14

  A convenient synthetic approach for previously unknown N-H imidoylphosphonates, based on addition of dialkyl phospites to trifluoroacetonitrile, was developed. Synthetic potentialities of imines 1 existing as equilibrium mixture of E/Z isomers, were demonstrated.

  开发了一种以前未知的 NH 亚氨基膦酸酯的便捷合成方法，该方法基于将二烷基亚磷酸酯添加到三氟乙腈中。证明了以 E/Z 异构体的平衡混合物形式存在的亚胺 1 的合成潜力。
• Fluorinated NH-iminophosphonates and iminocarboxylates: novel synthons for the preparation of biorelevant α-aminophosphonates and carboxylates
  作者：Yuliya V. Rassukana、Ivanna P. Yelenich、Anatoly D. Synytsya、Petro P. Onys'ko

  DOI：10.1016/j.tet.2014.03.030

  日期：2014.5

  A convenient synthetic approach to previously unknown N-H alpha-iminophosphonates and iminotrifluoropropionates was developed. The synthetic potential of N-H iminophosphonates and iminotrifluoropropionates, existing as an equilibrium mixture of E/Z-isomers, was demonstrated by their easy functionalization to afford biorelevant fluorinated alpha-aminophosphonic and alpha-aminocarboxylic acid derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• Fluorinated N‒H Imidoyl Phosphonates: Novel Synthones for the Preparation of Biorelevant α-Aminophosphonic Acid Derivatives
  作者：Y. V. Rassukana、I. P. Yelenich、P. P. Onys’ko、A. D. Synytsya

  DOI：10.1080/10426507.2012.743143

  日期：2013.1.1

  A convenient synthetic approach for previously unknown NH imidoyl phosphonates, based on addition of hydrophosphoryl compounds to fluorinated acetonitriles, was developed. The synthetic potential of NH imidoyl phosphonates, which exist as equilibrium mixture of E/Z isomers, was demonstrated by their easy functionalization to afford biorelevant derivatives of fluorinated -aminophosphonic acids.
• A New Strategy for Synthesis of Compounds Bearing Biorelevant α-Aminophosphonate Functionalities
  作者：Petro P. Onys’ko、Yuliya. V. Rassukana、Yaroslav Y. Khomutnyk、Ivanna P. Yelenich、Denys V. Klukovsky、Anatoly D. Synytsya

  DOI：10.1080/10426507.2014.974098

  日期：2015.6.3

  A novel strategy for synthesis of biorelevant alpha-aminophosphonic acid derivatives, based on the use of alpha-iminophosphonates as starting materials, was developed.