3-[2-[bis[2-[[3-[methyl(phenylmethoxy)amino]-3-oxopropyl]carbamoylamino]ethyl]amino]ethylcarbamoylamino]-N-methyl-N-phenylmethoxypropanamide | 1414689-52-3

• 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: 3-[2-[bis[2-[[3-[methyl(phenylmethoxy)amino]-3-oxopropyl]carbamoylamino]ethyl]amino]ethylcarbamoylamino]-N-methyl-N-phenylmethoxypropanamide
• CAS: 1414689-52-3
• 化学式: C₄₂H₆₀N₁₀O₉
• 分子量: 849.0
• InChiKey: ONNRQPDJXGYWTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  61
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  215
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[2-[bis[2-[[3-[methyl(phenylmethoxy)amino]-3-oxopropyl]carbamoylamino]ethyl]amino]ethylcarbamoylamino]-N-methyl-N-phenylmethoxypropanamide 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到3-[2-[bis[2-[[3-[hydroxy(methyl)amino]-3-oxopropyl]carbamoylamino]ethyl]amino]ethylcarbamoylamino]-N-hydroxy-N-methylpropanamide
  参考文献：
  名称：

  Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators

  摘要：

  Two novel bifunctional N-methylhydroxamate-isocyanate linkers 20 and 21 were prepared in good yield and high purity from the corresponding amine salts using a biphasic reaction with phosgene. The facile ring opening reaction of N-Boc lactams using the anion of O-benzylhydroxylamine gave the protected amino hydroxamates 6a and 6c in good yields. The selective methylation of the hydroxamate nitrogen in the presence of the N-Boc group in these intermediates could be readily accomplished. The utility of the linkers was clearly demonstrated by the synthesis of the carbamate-tethered trishydroxamic acid 27 and the urea-tethered 29. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.025
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 3-[2-[bis[2-[[3-[methyl(phenylmethoxy)amino]-3-oxopropyl]carbamoylamino]ethyl]amino]ethylcarbamoylamino]-N-methyl-N-phenylmethoxypropanamide
  参考文献：
  名称：

  Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators

  摘要：

  Two novel bifunctional N-methylhydroxamate-isocyanate linkers 20 and 21 were prepared in good yield and high purity from the corresponding amine salts using a biphasic reaction with phosgene. The facile ring opening reaction of N-Boc lactams using the anion of O-benzylhydroxylamine gave the protected amino hydroxamates 6a and 6c in good yields. The selective methylation of the hydroxamate nitrogen in the presence of the N-Boc group in these intermediates could be readily accomplished. The utility of the linkers was clearly demonstrated by the synthesis of the carbamate-tethered trishydroxamic acid 27 and the urea-tethered 29. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.025

文献信息

• Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators
  作者：Rasika Fernando、Jonathan M. Shirley、Emilio Torres、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tetlet.2012.09.025

  日期：2012.11

  Two novel bifunctional N-methylhydroxamate-isocyanate linkers 20 and 21 were prepared in good yield and high purity from the corresponding amine salts using a biphasic reaction with phosgene. The facile ring opening reaction of N-Boc lactams using the anion of O-benzylhydroxylamine gave the protected amino hydroxamates 6a and 6c in good yields. The selective methylation of the hydroxamate nitrogen in the presence of the N-Boc group in these intermediates could be readily accomplished. The utility of the linkers was clearly demonstrated by the synthesis of the carbamate-tethered trishydroxamic acid 27 and the urea-tethered 29. (C) 2012 Elsevier Ltd. All rights reserved.