4,5-dimethoxy-2-nitrobenzyl 2-propynylcarbamate | 431042-66-9

• 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: 4,5-dimethoxy-2-nitrobenzyl 2-propynylcarbamate
• 英文别名: 4,5-Dimethoxy-2-nitrobenzyl prop-2-yn-1-ylcarbamate；(4,5-dimethoxy-2-nitrophenyl)methyl N-prop-2-ynylcarbamate
• CAS: 431042-66-9
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: FWOUQVDBCOVJFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-nitrobenzyl 2-propynylcarbamate 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 N-(2-Boc-aminoethyl)-N-{5-[3-([(4,5-dimethoxy-2-nitrobenzyl)oxycarbonyl]amino)-1-propynyl]uracil-1-yl}acetyl glycine
  参考文献：
  名称：

  The use of Sonogashira coupling for the synthesis of modified uracil peptide nucleic acid

  摘要：

  Palladium-catalyzed Sonogashira coupling has been shown to be compatible with PNA monomers as illustrated by the reaction of 5-iodouracil peptide nucleic acid monomer (U-1-PNA) with several terminal alkynes. These reactions hake been performed in the solution Phase and with U-1-PNA linked to an insoluble polymer Support. The results presented herein shock that while the isolated yields from the solution phase chemistry are modest (38 53%), the yields of the resin-bound Coupling reactions are essentially quantitative. at the monomer level. A selection of alkynes LIS used to install various additional functionality on the uracil nucleobase, Examples of a hydroxyl, protected thiol and protected amino group are given. Further, an example of derivatization of a resin-bound oligomer with a single U-1 insert is given. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00024-2
• 作为产物：
  描述：

  三光气 、 4,5-二甲氧基-2-硝基苯甲醇 、 炔丙胺 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 4,5-dimethoxy-2-nitrobenzyl 2-propynylcarbamate
  参考文献：
  名称：

  The use of Sonogashira coupling for the synthesis of modified uracil peptide nucleic acid

  摘要：

  Palladium-catalyzed Sonogashira coupling has been shown to be compatible with PNA monomers as illustrated by the reaction of 5-iodouracil peptide nucleic acid monomer (U-1-PNA) with several terminal alkynes. These reactions hake been performed in the solution Phase and with U-1-PNA linked to an insoluble polymer Support. The results presented herein shock that while the isolated yields from the solution phase chemistry are modest (38 53%), the yields of the resin-bound Coupling reactions are essentially quantitative. at the monomer level. A selection of alkynes LIS used to install various additional functionality on the uracil nucleobase, Examples of a hydroxyl, protected thiol and protected amino group are given. Further, an example of derivatization of a resin-bound oligomer with a single U-1 insert is given. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00024-2