di-tert-butyl 4-(2-tert-butoxycarbonylethyl)-4-(3-docosylureido)heptanedioate | 935676-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: di-tert-butyl 4-(2-tert-butoxycarbonylethyl)-4-(3-docosylureido)heptanedioate
• 英文别名: Ditert-butyl 4-(docosylcarbamoylamino)-4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]heptanedioate
• CAS: 935676-82-7
• 化学式: C₄₅H₈₆N₂O₇
• 分子量: 767.187
• InChiKey: ZPPOHIKRGRVVHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  54
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 4-(2-tert-butoxycarbonylethyl)-4-(3-docosylureido)heptanedioate 在 甲酸 作用下， 反应 9.0h， 生成 4-(2-carboxyethyl)-4-(3-docosylureido)heptanedioic acid
  参考文献：
  名称：

  Synthesis, Critical Micelle Concentrations, and Antimycobacterial Properties of Homologous, Dendritic Amphiphiles. Probing Intrinsic Activity and the “Cutoff” Effect

  摘要：

  Newkome-type, 1 -> 3 C-branched dendrons make an excellent headgroup for amphiphiles with ultralong, saturated, linear alkyl chains. Synthesis of a homologous series of five such amphiphiles from 14 to 22 carbonsRNHCONHC(CH2CH2CO2H)(3), R = n-CnH2n+1, n = 14, 16, 18, 20, 22proceeds readily. These amphiphiles are soluble in aqueous solutions of triethanolamine. Surface-tension measurements on this homologous series reveal an unusually gradual decrease in log critical micelle concentration (CMC) as the chain length increases. In fact, the tetradecyl homologue does not appear to form micelles. Further, measurements of minimal inhibitory concentration (MIC) by broth microdilution against Mycobacterium smegmatis as a function of the initial cell density provide a direct measure of the intrinsic activity (MIC0) of each homologue. The hexadecyl homologue is the most active at inhibiting growth with an MIC0 equal to 3.5 x 10(-5) M, which is 100-fold below the CMC.

  DOI：

  10.1021/jm061240d
• 作为产物：
  描述：

  二十二烷-1-醇 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、427.48 kPa 条件下， 反应 10.0h， 生成 di-tert-butyl 4-(2-tert-butoxycarbonylethyl)-4-(3-docosylureido)heptanedioate
  参考文献：
  名称：

  Synthesis, Critical Micelle Concentrations, and Antimycobacterial Properties of Homologous, Dendritic Amphiphiles. Probing Intrinsic Activity and the “Cutoff” Effect

  摘要：

  Newkome-type, 1 -> 3 C-branched dendrons make an excellent headgroup for amphiphiles with ultralong, saturated, linear alkyl chains. Synthesis of a homologous series of five such amphiphiles from 14 to 22 carbonsRNHCONHC(CH2CH2CO2H)(3), R = n-CnH2n+1, n = 14, 16, 18, 20, 22proceeds readily. These amphiphiles are soluble in aqueous solutions of triethanolamine. Surface-tension measurements on this homologous series reveal an unusually gradual decrease in log critical micelle concentration (CMC) as the chain length increases. In fact, the tetradecyl homologue does not appear to form micelles. Further, measurements of minimal inhibitory concentration (MIC) by broth microdilution against Mycobacterium smegmatis as a function of the initial cell density provide a direct measure of the intrinsic activity (MIC0) of each homologue. The hexadecyl homologue is the most active at inhibiting growth with an MIC0 equal to 3.5 x 10(-5) M, which is 100-fold below the CMC.

  DOI：

  10.1021/jm061240d

文献信息

• Synthesis, Critical Micelle Concentrations, and Antimycobacterial Properties of Homologous, Dendritic Amphiphiles. Probing Intrinsic Activity and the “Cutoff” Effect
  作者：Eko W. Sugandhi、Richard V. Macri、André A. Williams、Brett L. Kite、Carla Slebodnick、Joseph O. Falkinham、Alan R. Esker、Richard D. Gandour

  DOI：10.1021/jm061240d

  日期：2007.4.1

  Newkome-type, 1 -> 3 C-branched dendrons make an excellent headgroup for amphiphiles with ultralong, saturated, linear alkyl chains. Synthesis of a homologous series of five such amphiphiles from 14 to 22 carbonsRNHCONHC(CH2CH2CO2H)(3), R = n-CnH2n+1, n = 14, 16, 18, 20, 22proceeds readily. These amphiphiles are soluble in aqueous solutions of triethanolamine. Surface-tension measurements on this homologous series reveal an unusually gradual decrease in log critical micelle concentration (CMC) as the chain length increases. In fact, the tetradecyl homologue does not appear to form micelles. Further, measurements of minimal inhibitory concentration (MIC) by broth microdilution against Mycobacterium smegmatis as a function of the initial cell density provide a direct measure of the intrinsic activity (MIC0) of each homologue. The hexadecyl homologue is the most active at inhibiting growth with an MIC0 equal to 3.5 x 10(-5) M, which is 100-fold below the CMC.