Ethyl hydrogen4-(phthalimido)butylphosphonate | 405116-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Ethyl hydrogen4-(phthalimido)butylphosphonate
• 英文别名: 4-(1,3-dioxoisoindol-2-yl)butyl-ethoxyphosphinic acid
• CAS: 405116-81-6
• 化学式: C₁₄H₁₈NO₅P
• 分子量: 311.274
• InChiKey: BKSQTRSOZDSHIO-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±47.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl hydrogen4-(phthalimido)butylphosphonate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2-[4-[Ethoxy-(4-nitrophenoxy)-oxidophosphaniumyl]butyl]isoindole-1,3-dione
  参考文献：
  名称：

  A general synthesis of ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates

  摘要：

  Diethyl phosphonates were conveniently converted into ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates as potentially useful intermediates for the preparation of functionalized phenyl phosponates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02100-1
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Ethyl hydrogen4-(phthalimido)butylphosphonate
  参考文献：
  名称：

  A general synthesis of ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates

  摘要：

  Diethyl phosphonates were conveniently converted into ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates as potentially useful intermediates for the preparation of functionalized phenyl phosponates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02100-1

文献信息

• 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.
• A general synthesis of ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates
  作者：Stanislav Gobec、Katja Štrancar、Uroš Urleb

  DOI：10.1016/s0040-4039(01)02100-1

  日期：2002.1

  Diethyl phosphonates were conveniently converted into ethyl 4-aminophenyl and ethyl 4-[amino(hydroxyimino)methyl]phenyl phosphonates as potentially useful intermediates for the preparation of functionalized phenyl phosponates. (C) 2001 Elsevier Science Ltd. All rights reserved.