ethyl 4-(4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)benzyloxy)-3-nitrobenzoate | 1241948-96-8

• 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: ethyl 4-(4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)benzyloxy)-3-nitrobenzoate
• 英文别名: Ethyl 4-[[3-[benzyl(ethyl)amino]-4-[(3-methoxy-4-prop-2-enoxyphenyl)methoxy]phenyl]methoxy]-3-nitrobenzoate
• CAS: 1241948-96-8
• 化学式: C₃₆H₃₈N₂O₈
• 分子量: 626.706
• InChiKey: LXKOMMKUBQNMOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)benzyloxy)-3-nitrobenzoate 在 sodium tetrahydroborate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 以74%的产率得到ethyl 3-amino-4-(4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)benzyloxy)benzoate
  参考文献：
  名称：

  Improved Iterative Synthesis of Linearly Disassembling Dendrons

  摘要：

  We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first-through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the ally] trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.

  DOI：

  10.1021/jo1009849
• 作为产物：
  描述：

  4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)-benzyl alcohol 、 4-羟基-3-硝基苯甲酸乙酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到ethyl 4-(4-(4-allyloxy-3-methoxybenzyloxy)-3-(N-benzyl-N-ethylamino)benzyloxy)-3-nitrobenzoate
  参考文献：
  名称：

  Improved Iterative Synthesis of Linearly Disassembling Dendrons

  摘要：

  We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first-through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the ally] trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.

  DOI：

  10.1021/jo1009849

文献信息

• Improved Iterative Synthesis of Linearly Disassembling Dendrons
  作者：Adrian Ortiz、Charles S. Shanahan、David T. Sisk、Sujeewa C. Perera、Pallavi Rao、Dominic V. McGrath

  DOI：10.1021/jo1009849

  日期：2010.9.17

  We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first-through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the ally] trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.