4-(2-(2-环己基乙酰基)苯氧基)-3-硝基苯甲酸甲酯 | 1414926-66-1

• 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: 4-(2-(2-环己基乙酰基)苯氧基)-3-硝基苯甲酸甲酯
• 英文名称: methyl 4-(2-(2-cyclohexylacetyl)phenoxy)-3-nitrobenzoate
• CAS: 1414926-66-1
• 化学式: C₂₂H₂₃NO₆
• 分子量: 397.428
• InChiKey: IXBVIDAEHFPXLM-UHFFFAOYSA-N

物化性质

• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2-(2-环己基乙酰基)苯氧基)-3-硝基苯甲酸甲酯 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以42.5%的产率得到4-[1-cyclohexyl-2-(2-hydroxy-phenyl)-2-oxo-ethyl]-3-nitrobenzoic acid methyl ester
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p
• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 在 甲烷磺酸 、 氢溴酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 正庚烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 4-(2-(2-环己基乙酰基)苯氧基)-3-硝基苯甲酸甲酯
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p