methyl 4-(2-oxo-1,2,2',4'-tetrahydrospiro[indole-3,3'-pyrazol]-5'-yl)phenylcarbamate | 1267436-50-9

• 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: methyl 4-(2-oxo-1,2,2',4'-tetrahydrospiro[indole-3,3'-pyrazol]-5'-yl)phenylcarbamate
• 英文别名: 5'-(4-Methoxycarbonylaminophenyl)-2',4'-dihydrospiro[indole-3,3'-pyrazol]-2(1h)-one；methyl N-[4-(2'-oxospiro[1,4-dihydropyrazole-5,3'-1H-indole]-3-yl)phenyl]carbamate
• CAS: 1267436-50-9
• 化学式: C₁₈H₁₆N₄O₃
• 分子量: 336.35
• InChiKey: LAZKSKZRKSDBFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl N-{4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetyl]phenyl}carbamate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以95%的产率得到methyl 4-(2-oxo-1,2,2',4'-tetrahydrospiro[indole-3,3'-pyrazol]-5'-yl)phenylcarbamate
  参考文献：
  名称：

  Synthesis of new spiro compounds containing a carbamate group

  摘要：

  1,3-Dipolar cycloaddition to methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]-phenylcarbamate of diazomethane in chloroform-diethyl ether and of 3,4-dimethoxybenzonitrile oxide generated from the corresponding aldehyde oxime by the action of N-chlorobenzenesulfonamide sodium salt (Chloramine B) in boiling ethanol gave, respectively, methyl 4-(2-oxo-1',5'-dihydro-1H-spiro[indole-3,4'-pyrazol]-3'-ylcarbonyl)phenylcarbamate and methyl 4-[3'-(3,4-dimethoxyphenyl)-2-oxo-1H,4'H-spiro[indole-3,5'-isoxazol]-4'-ylcarbonyl]phenylcarbamate. The condensation of methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]phenylcarbamate with hydrazine hydrate in ethanol afforded methyl 4-(2-oxo-1,2,2',4'-tetrahydrospiro[indole-3,3'-pyrazol]-5'-yl)phenylcarbamate.

  DOI：

  10.1134/s1070428010120092

文献信息

• Synthesis of new spiro compounds containing a carbamate group
  作者：A. V. Velikorodov、O. Yu. Poddubnyi、A. K. Kuanchalieva、O. O. Krivosheev

  DOI：10.1134/s1070428010120092

  日期：2010.12

  1,3-Dipolar cycloaddition to methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]-phenylcarbamate of diazomethane in chloroform-diethyl ether and of 3,4-dimethoxybenzonitrile oxide generated from the corresponding aldehyde oxime by the action of N-chlorobenzenesulfonamide sodium salt (Chloramine B) in boiling ethanol gave, respectively, methyl 4-(2-oxo-1',5'-dihydro-1H-spiro[indole-3,4'-pyrazol]-3'-ylcarbonyl)phenylcarbamate and methyl 4-[3'-(3,4-dimethoxyphenyl)-2-oxo-1H,4'H-spiro[indole-3,5'-isoxazol]-4'-ylcarbonyl]phenylcarbamate. The condensation of methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]phenylcarbamate with hydrazine hydrate in ethanol afforded methyl 4-(2-oxo-1,2,2',4'-tetrahydrospiro[indole-3,3'-pyrazol]-5'-yl)phenylcarbamate.