4-benzyloxy-2-methyl-5-(1-methylethyl)nitrobenzene | 159388-65-5

• 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-benzyloxy-2-methyl-5-(1-methylethyl)nitrobenzene
• 英文别名: 1-Methyl-2-nitro-5-phenylmethoxy-4-propan-2-ylbenzene
• CAS: 159388-65-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: AQXQAFQXUZRFFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2-methyl-5-(1-methylethyl)nitrobenzene 在 palladium on activated charcoal 、 镍 氢氧化钾 、 氢气 、 苄基三丁基氯化铵 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0~110.0 ℃ 、172.37 kPa 条件下， 反应 20.5h， 生成 5-<2-<4-(2-methoxyphenyl)-1-piperazinyl>ethoxy>-1-methyl-6-(1-methylethyl)indole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new indole derivatives structurally related to thymoxamine

  摘要：

  The synthesis and pharmacological evaluation of a series of pyrrolidine analogues of thymoxamine allowed access to the basic SAR for the aromatic substitution pattern. The results confirm the relevance of the simultaneous presence of the hydroxy and methyl groups on the benzene ring and prompted us to prepare the corresponding indole congener. The principle of the phenol-indol bioisosterism was confirmed by the results obtained. The introduction of the N-(2 methoxyphenyl)piperazine moiety instead of pyrrolidine changed the receptor affinity profile and introduced a good uroselectivity.

  DOI：

  10.1016/0223-5234(94)90147-3
• 作为产物：
  描述：

  5-甲基-2-(1-甲基乙基)4-硝基苯酚 、 氯化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以96%的产率得到4-benzyloxy-2-methyl-5-(1-methylethyl)nitrobenzene
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new indole derivatives structurally related to thymoxamine

  摘要：

  The synthesis and pharmacological evaluation of a series of pyrrolidine analogues of thymoxamine allowed access to the basic SAR for the aromatic substitution pattern. The results confirm the relevance of the simultaneous presence of the hydroxy and methyl groups on the benzene ring and prompted us to prepare the corresponding indole congener. The principle of the phenol-indol bioisosterism was confirmed by the results obtained. The introduction of the N-(2 methoxyphenyl)piperazine moiety instead of pyrrolidine changed the receptor affinity profile and introduced a good uroselectivity.

  DOI：

  10.1016/0223-5234(94)90147-3

文献信息

• Synthesis and pharmacological evaluation of new indole derivatives structurally related to thymoxamine
  作者：A Leonardi、C Riva、C De Toma、C Boi、R Pennini、G Sironi

  DOI：10.1016/0223-5234(94)90147-3

  日期：1994.1

  The synthesis and pharmacological evaluation of a series of pyrrolidine analogues of thymoxamine allowed access to the basic SAR for the aromatic substitution pattern. The results confirm the relevance of the simultaneous presence of the hydroxy and methyl groups on the benzene ring and prompted us to prepare the corresponding indole congener. The principle of the phenol-indol bioisosterism was confirmed by the results obtained. The introduction of the N-(2 methoxyphenyl)piperazine moiety instead of pyrrolidine changed the receptor affinity profile and introduced a good uroselectivity.