phenethylphosphonic acid monoethyl ester | 14295-50-2

• 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: phenethylphosphonic acid monoethyl ester
• 英文别名: Ethoxy(phenethyl)phosphinic acid；ethoxy(2-phenylethyl)phosphinic acid
• CAS: 14295-50-2
• 化学式: C₁₀H₁₅O₃P
• 分子量: 214.201
• InChiKey: GZUDEZNVOZREBO-UHFFFAOYSA-N

物化性质

• 沸点：
  340.0±35.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenethylphosphonic acid monoethyl ester 、 N-羟甲基邻苯二甲酰亚胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71.9%的产率得到(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl ethyl phenethylphosphonate
  参考文献：
  名称：

  Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall

  摘要：

  Phosphonate inhibitors of antigen 85C were prepared. The inhibitors, comprising a phosphonate moiety, mycolic acid mimetic and a trehalose surrogate, contain substituted benzyl alcohols, N-(omega-hydroxyalky)phthalimide, 2-phenylethanol or 4-(phthalimido)butanol as trehalose mimetics, and an alkyl chain of different lengths mimicking the mycolic acid side chain. The best compounds inhibited the mycolyltransferase activity of antigen 85C With IC50 in the low micromolar range and inhibited the growth of Mycobacterium avium in culture. The best compounds in the 3-phenoxybenzyl- and omega-(phthalimido)alkoxy series, ethyl 3-phenoxybenzyl butylphosphonate (4a) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) methyl ethyl heptylphosphonate (5c) displayed IC50 values of 2.0 and 1.3 mu M, respectively, in a mycolyltransferase inhibition assay. In a M. avium growth inhibition assay MIC of 4a and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate (5d) were 248.8 and 84.5 mu g/mL, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.08.007
• 作为产物：
  描述：

  2-苯基乙基磷酸二乙酯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 phenethylphosphonic acid monoethyl ester
  参考文献：
  名称：

  Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall

  摘要：

  Phosphonate inhibitors of antigen 85C were prepared. The inhibitors, comprising a phosphonate moiety, mycolic acid mimetic and a trehalose surrogate, contain substituted benzyl alcohols, N-(omega-hydroxyalky)phthalimide, 2-phenylethanol or 4-(phthalimido)butanol as trehalose mimetics, and an alkyl chain of different lengths mimicking the mycolic acid side chain. The best compounds inhibited the mycolyltransferase activity of antigen 85C With IC50 in the low micromolar range and inhibited the growth of Mycobacterium avium in culture. The best compounds in the 3-phenoxybenzyl- and omega-(phthalimido)alkoxy series, ethyl 3-phenoxybenzyl butylphosphonate (4a) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) methyl ethyl heptylphosphonate (5c) displayed IC50 values of 2.0 and 1.3 mu M, respectively, in a mycolyltransferase inhibition assay. In a M. avium growth inhibition assay MIC of 4a and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate (5d) were 248.8 and 84.5 mu g/mL, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.08.007

文献信息

• Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
  作者：Nikoletta Harsági、Zita Rádai、Áron Szigetvári、János Kóti、György Keglevich

  DOI：10.3390/molecules25173793

  日期：——

  acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The

  监测 α-羟基苄基膦酸酯和一些相关衍生物的两步酸性水解，以确定动力学并绘制不同取代的膦酸酯在水解中的反应性。吸电子取代基增加了速率，而放电子取代基减慢了反应速度。两个水解步骤都以伪一级速率常数为特征。发现第二个 POC 键的裂变是决定速率的步骤。
• Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall
  作者：Stanislav Gobec、Ivan Plantan、Janez Mravljak、Urban Švajger、Rosalind A. Wilson、Gurdyal S. Besra、Sousana L. Soares、Rui Appelberg、Danijel Kikelj

  DOI：10.1016/j.ejmech.2006.08.007

  日期：2007.1

  Phosphonate inhibitors of antigen 85C were prepared. The inhibitors, comprising a phosphonate moiety, mycolic acid mimetic and a trehalose surrogate, contain substituted benzyl alcohols, N-(omega-hydroxyalky)phthalimide, 2-phenylethanol or 4-(phthalimido)butanol as trehalose mimetics, and an alkyl chain of different lengths mimicking the mycolic acid side chain. The best compounds inhibited the mycolyltransferase activity of antigen 85C With IC50 in the low micromolar range and inhibited the growth of Mycobacterium avium in culture. The best compounds in the 3-phenoxybenzyl- and omega-(phthalimido)alkoxy series, ethyl 3-phenoxybenzyl butylphosphonate (4a) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) methyl ethyl heptylphosphonate (5c) displayed IC50 values of 2.0 and 1.3 mu M, respectively, in a mycolyltransferase inhibition assay. In a M. avium growth inhibition assay MIC of 4a and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate (5d) were 248.8 and 84.5 mu g/mL, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.