methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-4-nitro-1H-indole-1-carboxylate | 1248342-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-4-nitro-1H-indole-1-carboxylate
• 英文别名: methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-4-nitroindole-1-carboxylate
• CAS: 1248342-17-7
• 化学式: C₁₅H₁₅N₃O₇
• 分子量: 349.3
• InChiKey: RGFVSPNDLQSYPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate 在 乙酸酐 、 copper(II) nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以58%的产率得到methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-4-nitro-1H-indole-1-carboxylate
  参考文献：
  名称：

  Synthesis of new carbamate derivatives of indole and their modification

  摘要：

  Oximation of indoles having a methoxycarbonylamino group on C(5) and an acyl group on C(3) with hydroxylamine hydrochloride in the presence of pyridine gave the corresponding oximes. The reduction of the 3-C=O group with sodium tetrahydridoborate in the presence of sodium hydroxide was accompanied by removal of the methoxycarbonyl group at the pyrrole nitrogen atom with formation of racemic alcohols. 1,4-Addition of 1-(pyridin-3-yl)butane-1,3-dione to dimethyl 1,4-benzoquinone diimine N,N'-dicarboxylate in dioxane in the presence of sodium methoxide, followed by heating in boiling 22% hydrochloric acid, afforded methyl 2-methyl-5-(methoxycarbonylamino)-3-(pyridin-3-ylcarbonyl)-1H-indole-1-carboxylate. 3-(Dimethylamino)-1-(4-methyl-1,2,5-oxadiazol-3-yl)prop-2-en-1-one reacted with N,N'-bis(methoxycarbonyl)- and N,N'-bis(phenylsulfonyl)-1,4-benzoquinone diimines in methylene chloride and acetic acid, respectively, in the presence of BF(3) center dot Et(2)O to produce indoles having a 1,2,5-oxadiazolylcarbonyl group on C(3).

  DOI：

  10.1134/s107042801007016x