3-acetamido-5-nitrobenzyl alcohol | 1018448-89-9

• 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: 3-acetamido-5-nitrobenzyl alcohol
• 英文别名: N-[3-(hydroxymethyl)-5-nitrophenyl]acetamide
• CAS: 1018448-89-9
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: SOVBBDHUNZQYHT-UHFFFAOYSA-N

物化性质

• 沸点：
  475.3±40.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetamido-5-nitrobenzyl alcohol 在 吡啶 、 咪唑 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of benzamide DNA minor groove binders

  摘要：

  A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.090
• 作为产物：
  描述：

  3-氨基-5-硝基苯甲醇 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3-acetamido-5-nitrobenzyl alcohol
  参考文献：
  名称：

  Synthesis and biological activity of benzamide DNA minor groove binders

  摘要：

  A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.090

文献信息

• Synthesis of non-symmetrical 3,5-diamidobenzyl amines, ethers and sulfides
  作者：David Barker、Anna L. Lehmann、Anna Mai、Gul S. Khan、Eric Ng

  DOI：10.1016/j.tetlet.2008.01.003

  日期：2008.3

  A straightforward synthesis of non-symmetrical 3,5-diamidobenzyl amines, ethers and sulfides starting from 3,5-dinitrobenzoic acid is reported. Functionalization of the benzylic position is only achieved after formation of the two amides, otherwise benzylic hydrogenolysis occurs during nitro group reduction.

  据报道，以3，5-二硝基苯甲酸为原料，可以直接合成不对称的3，5-二酰胺基苄基胺，醚和硫化物。苄基位置的官能化仅在两种酰胺形成后才能实现，否则在硝基还原过程中发生苄基氢解。