methyl-phosphonic acid prop-2-ynyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester | 1347749-24-9

• 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: methyl-phosphonic acid prop-2-ynyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester
• 英文别名: 1,1,1,3,3,3-Hexafluoro-2-[methyl(prop-2-ynoxy)phosphoryl]oxypropane
• CAS: 1347749-24-9
• 化学式: C₇H₇F₆O₃P
• 分子量: 284.095
• InChiKey: XOWVPELMLPDDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-isoleucyl-N1-[(1S)-2-azido-1-methylethyl]-N2-(2,4-dimethoxybenzyl)-2-methylalaninamide 、 methyl-phosphonic acid prop-2-ynyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以56%的产率得到N-(tert-butoxycarbonyl)-L-isoleucyl-N2-(2,4-dimethoxybenzyl)-2-methyl-N1-((1S)-1-methyl-2-{4-[({methyl[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]phosphoryl}oxy)methyl]-1H-1,2,3-triazol-1-yl}ethyl)alaninamide
  参考文献：
  名称：

  Synthesis and testing of trifluoromethyl-containing phosphonate–peptide conjugates as inhibitors of serine hydrolases

  摘要：

  A modification of novel fluorinated organophosphorous compounds containing terminal alkyne group by different azidopeptides via Cu(I)-catalyzed click chemistry has been described. The inhibitor activity of trifluoromethyl-containing methylphosphonates and their peptide-conjugates towards acetylcholinesterase, butyrylcholinesterase, and carboxylesterase has been investigated. It was shown that the incorporation of peptide fragments significantly modulates the esterase profile of starting methylphosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.030
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以11 g的产率得到methyl-phosphonic acid prop-2-ynyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester
  参考文献：
  名称：

  Synthesis and testing of trifluoromethyl-containing phosphonate–peptide conjugates as inhibitors of serine hydrolases

  摘要：

  A modification of novel fluorinated organophosphorous compounds containing terminal alkyne group by different azidopeptides via Cu(I)-catalyzed click chemistry has been described. The inhibitor activity of trifluoromethyl-containing methylphosphonates and their peptide-conjugates towards acetylcholinesterase, butyrylcholinesterase, and carboxylesterase has been investigated. It was shown that the incorporation of peptide fragments significantly modulates the esterase profile of starting methylphosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.030

文献信息

• Synthesis and testing of trifluoromethyl-containing phosphonate–peptide conjugates as inhibitors of serine hydrolases
  作者：Nadezhda V. Sokolova、Valentine G. Nenajdenko、Vladimir B. Sokolov、Olga G. Serebryakova、Galina F. Makhaeva

  DOI：10.1016/j.bmcl.2011.09.030

  日期：2011.12

  A modification of novel fluorinated organophosphorous compounds containing terminal alkyne group by different azidopeptides via Cu(I)-catalyzed click chemistry has been described. The inhibitor activity of trifluoromethyl-containing methylphosphonates and their peptide-conjugates towards acetylcholinesterase, butyrylcholinesterase, and carboxylesterase has been investigated. It was shown that the incorporation of peptide fragments significantly modulates the esterase profile of starting methylphosphonates. (C) 2011 Elsevier Ltd. All rights reserved.