O,O'-diethyl [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate | 1251860-61-3

• 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: O,O'-diethyl [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate
• 英文别名: diethyl (2-{[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethyl)phosphonate；N-[3,5-bis(trifluoromethyl)phenyl]-2-[diethoxy(oxido)phosphaniumyl]acetamide
• CAS: 1251860-61-3
• 化学式: C₁₄H₁₆F₆NO₄P
• 分子量: 407.25
• InChiKey: PVSCGGYVBAFPHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O,O'-diethyl [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate 在 吡啶 、 三甲基溴硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and biological properties of α-thymidine 5′-aryl phosphonates

  摘要：

  Diethyl(N-arylaminocarbonyl)methyl phosphonates have been obtained by the reaction of diethylphosphonoacetic acid imidazolides with methyl-4-aminobenzoate or 3,5-bis(trifluoromethyl)phenylamine. Their treatment with Me3SiBr in DMF led to a mixture of the corresponding (N-arylaminocarbonylmethyl)phosphonic acids and their monoethyl esters. After separation, they were condensed with 3'-O-acetyl-alpha-thymidine, which, after the removal of the acetyl protecting group, gave (alpha-D-thymidine-5'-yl)-[4-aminocarbonyl-, methoxycarbonyl-, or carboxy)phenylaminocarbonyl]methyl phosphonates and (alpha-D-thymidine-5'-yl)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. It was shown that the compounds are stable under different conditions, low toxic (in Vero and K-562 cell cultures), and capable of penetrating into K-562 cells. Only ethyl (alpha-D-thymidine-5'-yl)-[4-(methoxycarbonyl)phenylaminocarbonyl]methyl phosphonate at a high concentration (200 mu g/mL) inhibited in vitro the growth of the laboratory strain M. tuberculosis H37Rv.

  DOI：

  10.1134/s1068162013060058
• 作为产物：
  描述：

  二乙基磷乙酸 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 O,O'-diethyl [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate
  参考文献：
  名称：

  Synthesis and biological properties of α-thymidine 5′-aryl phosphonates

  摘要：

  Diethyl(N-arylaminocarbonyl)methyl phosphonates have been obtained by the reaction of diethylphosphonoacetic acid imidazolides with methyl-4-aminobenzoate or 3,5-bis(trifluoromethyl)phenylamine. Their treatment with Me3SiBr in DMF led to a mixture of the corresponding (N-arylaminocarbonylmethyl)phosphonic acids and their monoethyl esters. After separation, they were condensed with 3'-O-acetyl-alpha-thymidine, which, after the removal of the acetyl protecting group, gave (alpha-D-thymidine-5'-yl)-[4-aminocarbonyl-, methoxycarbonyl-, or carboxy)phenylaminocarbonyl]methyl phosphonates and (alpha-D-thymidine-5'-yl)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. It was shown that the compounds are stable under different conditions, low toxic (in Vero and K-562 cell cultures), and capable of penetrating into K-562 cells. Only ethyl (alpha-D-thymidine-5'-yl)-[4-(methoxycarbonyl)phenylaminocarbonyl]methyl phosphonate at a high concentration (200 mu g/mL) inhibited in vitro the growth of the laboratory strain M. tuberculosis H37Rv.

  DOI：

  10.1134/s1068162013060058

文献信息

• Efficient method to prepare diethylphosphonacetamides
  作者：Federico Scaravelli、Sergio Bacchi、Luca Massari、Ornella Curcuruto、Pieter Westerduin、William Maton

  DOI：10.1016/j.tetlet.2010.07.125

  日期：2010.9

  An efficient and versatile synthetic method is described to synthesize diethylphosphonacetamides in a single step. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and biological properties of α-thymidine 5′-aryl phosphonates
  作者：M. A. Ivanov、I. L. Karpenko、L. N. Chernousova、S. N. Andreevskaya、T. G. Smirnova、L. A. Alexandrova

  DOI：10.1134/s1068162013060058

  日期：2013.11

  Diethyl(N-arylaminocarbonyl)methyl phosphonates have been obtained by the reaction of diethylphosphonoacetic acid imidazolides with methyl-4-aminobenzoate or 3,5-bis(trifluoromethyl)phenylamine. Their treatment with Me3SiBr in DMF led to a mixture of the corresponding (N-arylaminocarbonylmethyl)phosphonic acids and their monoethyl esters. After separation, they were condensed with 3'-O-acetyl-alpha-thymidine, which, after the removal of the acetyl protecting group, gave (alpha-D-thymidine-5'-yl)-[4-aminocarbonyl-, methoxycarbonyl-, or carboxy)phenylaminocarbonyl]methyl phosphonates and (alpha-D-thymidine-5'-yl)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. It was shown that the compounds are stable under different conditions, low toxic (in Vero and K-562 cell cultures), and capable of penetrating into K-562 cells. Only ethyl (alpha-D-thymidine-5'-yl)-[4-(methoxycarbonyl)phenylaminocarbonyl]methyl phosphonate at a high concentration (200 mu g/mL) inhibited in vitro the growth of the laboratory strain M. tuberculosis H37Rv.