methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate
• 英文别名: methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-1H-indole-1-carboxylate；Methyl 3-acetyl-5-(methoxycarbonylamino)-2-methyl-indole-1-carboxylate；methyl 3-acetyl-5-(methoxycarbonylamino)-2-methylindole-1-carboxylate
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: VRADNRJZOPYSEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 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：
  86.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以87%的产率得到methyl 5-[(methoxycarbonyl)amino]-2-methyl-3-(2-oxoacetyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  3-乙酰基-5-[（甲氧基羰基）氨基] -2-甲基-1 H-吲哚-1-羧酸甲酯的官能化

  摘要：

  二氧化硒在乙酸和乙酸中的作用下，氧化3- {1- [2- [氨基甲酰基肼基亚乙基]]乙基} -2-甲基-5-[（甲氧羰基）氨基] -1 H-吲哚-1-羧酸甲酯的杂环在沸腾的乙酸酐中加热相应的硫代半脲，分别得到1,2,3-硒代二唑和2,3-二氢-1,3,4-噻二唑衍生物。3-乙酰基-2-甲基-5-[（甲氧基羰基）氨基] -1 H-吲哚-1-甲酸甲酯与二氧化硒在二恶烷-水（30：1）中在80‒90°C下反应形成甲基5- [（甲氧基羰基）氨基] -2-甲基-3-（2-氧代乙酰基）-1 H-吲哚-1-羧酸酯，与邻苯二胺缩合，得到2-甲基-5-[（甲氧基羰基）氨基] -3-甲基（喹喔啉-2-基）-1 H-吲哚-1-羧酸酯。

  DOI：

  10.1134/s1070428016060129
• 作为产物：
  描述：

  [3-(1-Acetyl-2-oxo-propyl)-4-methoxycarbonylamino-phenyl]-carbamic acid methyl ester 在 盐酸 作用下， 以94%的产率得到methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate
  参考文献：
  名称：

  Velikorodov; Mochalin, Russian Journal of Organic Chemistry, 1998, vol. 34, # 10, p. 1490 - 1493

  摘要：

  DOI：

文献信息

• Synthesis of new carbamate derivatives of indole and their modification
  作者：A. V. Velikorodov、A. K. Kuanchalieva、O. L. Titova

  DOI：10.1134/s107042801007016x

  日期：2010.7

  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).
• Nenitzescu synthesis of carbamate indole derivatives from N,N′-bis(methoxycarbonyl)-p-benzoquinone diimine
  作者：A. M. Borisov、N. A. Kamanina、A. V. Velikorodov

  DOI：10.1134/s1070428007030141

  日期：2007.3

  N,N'-B s(methoxycarbonyl)-p-benzoquinone diimine reacted with 4-(cyclohex-1-en-1-yl)- and 4-(cyclopent-1-en-1-yl)morpholines in methylene chloride at room temperature to give morpholino-substituted cyclohexane- and cyclopentane-fused indole derivatives. Heating of the latter in boiling 10% hydrochloric acid led to the formation of methyl 6-(methoxycarbonylamino)-1,2,3,4,4a,9a-hexahydro-9H-carbazole-9-carboxylate and methyl 7 -(methoxycarbonylamino)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-4-carboxylate, respectively. The reaction of N,N'-bis(methoxycarbonyl)-p-benzoquinone diimine with 4-benzylaminopent-3-en-2-one in CH2Cl2 in the presence of BF3 center dot Et2O on heating gave methyl 3-acetyl-2-methyl-(5-methoxy-carbonylamino)-1H-indole-1-carboxylate.