2-羟基-N-[5-[(2-羟基苯甲酰基)氨基]戊基]苯甲酰胺 | 129944-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-N-[5-[(2-羟基苯甲酰基)氨基]戊基]苯甲酰胺
• 英文名称: N,N'-Bis(2-hydroxybenzoyl)-1,5-diaminopentane
• 英文别名: 1,2-bis(2-hydroxybenzamido)pentane；Benzamide, N,N'-1,5-pentanediylbis(2-hydroxy-；2-hydroxy-N-[5-[(2-hydroxybenzoyl)amino]pentyl]benzamide
• CAS: 129944-85-0
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: PYVNJYHJVKTEIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-N-[5-[(2-羟基苯甲酰基)氨基]戊基]苯甲酰胺 、 二氯乙醚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到
  参考文献：
  名称：

  A Convenient Method for Preparing Some New Macrocyclic Diamides

  摘要：

  开发了一种简单方便的方法，用于制备包含两个硫原子或两个到四个氧原子的不同环尺寸的宏环二酰胺。该两步法仅由反应水杨酸或2-巯基苯甲酸与各种二胺组成，随后进行威廉逊合成。

  DOI：

  10.1055/s-1994-25466
• 作为产物：
  描述：

  1,5-二氨基戊烷 、 水杨酸苯酯 反应 1.5h， 以30%的产率得到2-羟基-N-[5-[(2-羟基苯甲酰基)氨基]戊基]苯甲酰胺
  参考文献：
  名称：

  Daidone; Raffa; Maggio, Il Farmaco, 1990, vol. 45, # 3, p. 285 - 292

  摘要：

  DOI：

文献信息

• Synthesis and characterization of a family of binuclear non-heme iron monooxygenase model compounds: Evidence for a “phenolate/amide carbonyl (PAC) shift” upon oxidation
  作者：Patrick J. Cappillino、Paul C. Tarves、Gerard T. Rowe、Andrew J. Lewis、Mark Harvey、Corina Rogge、Adonis Stassinopoulos、Wayne Lo、William H. Armstrong、John P. Caradonna

  DOI：10.1016/j.ica.2008.09.036

  日期：2009.5

  A series of binuclear iron compounds has been synthesized using diamide, bis-phenolate ligands in which the carbon-linker between the amide nitrogen atoms has been varied. Two diferrous compounds in the series, Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) along with their two-electron oxidized, di-mu-methoxy-bridged counterparts, Fe-III(H(2)Hbach)(2)(OMe)(2) and Fe-III(H(2)Hbame)(2)(OMe)(2) have been crystallographically characterized, as have the di-mu-methoxy compounds Fe-2(III)(H(2)Hbap)(2)(OMe)(2); Fe-2(III)(H(2)Hbabn)(2)(OMe)(2) and Fe-2(III)(H(2)Hbapen)(2)(OMe)(2) (H(2)Hbab = 1,2-bis(2-hydroxybenzamido) benzene, H(2)Hbach = trans-1,2-bis(2-hydroxybenzamido) cyclohexane, H(2)Hbame = 1,2-bis(2-hydroxybenzamido) ethane, H(2)Hbap = 1,3-bis(2-hydroxybenzamido) propane, H(2)Hbabn = 1,4-bis(2-hydroxybenzamido) butane, H(2)Hbapen = 1,5-bis(2-hydroxybenzamido) pentane, N-MeIM = N-methylimidazole and OMe = methoxide). Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) are structurally very similar to previously reported diferrous compounds of this family of ligands that have been shown to be active as oxygen atom transfer catalysts. Flexibility in the carbon-linker allows some variability in the orientation of the phenolate arms of the ligands in the diferric di-mu-methoxy compounds, but the Fe2O2 core remains largely unchanged across the series. Two-electron oxidation of the ferrous compounds in methanol shows a substantial ligand rearrangement that is consistent with other spectroscopic, electrochemical and kinetic investigations. The loss of both phenolate bridges upon oxidation is reminiscent of the "carboxylate shift" observed in binuclear non-heme enzymes and could provide insight into the driving force behind this family of compounds' function as a catalyst. (c) 2008 Elsevier B. V. All rights reserved.
• A Convenient Method for Preparing Some New Macrocyclic Diamides
  作者：Lilian Kao Liu、Tsing-Pai Hsieh、Sung-Ming Kuo

  DOI：10.1055/s-1994-25466

  日期：——

  A simple and convenient method for preparing macrocyclic diamides containing two sulfur atoms or two to four oxygen atoms of various ring sizes was developed. This two-step procedure is simply composed of reacting salicyclic acid or 2-mercaptobenzoic acid with various diamines, followed by a Williamson synthesis.

  开发了一种简单方便的方法，用于制备包含两个硫原子或两个到四个氧原子的不同环尺寸的宏环二酰胺。该两步法仅由反应水杨酸或2-巯基苯甲酸与各种二胺组成，随后进行威廉逊合成。
• Daidone; Raffa; Maggio, Il Farmaco, 1990, vol. 45, # 3, p. 285 - 292
  作者：Daidone、Raffa、Maggio、Plescia、Matera Caruso

  DOI：——

  日期：——