1-isopropyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile | 1421005-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-isopropyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
• 英文别名: 1-propan-2-yl-3-sulfanylidene-5,6,7,8-tetrahydro-2H-isoquinoline-4-carbonitrile
• CAS: 1421005-83-5
• 化学式: C₁₃H₁₆N₂S
• 分子量: 232.349
• InChiKey: YKZSABDGFXJKDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(溴乙酰基)香豆素 、 1-isopropyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以71%的产率得到1-isopropyl-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethylsulfanyl]-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile
  参考文献：
  名称：

  Synthesis and alkylation of 1-substituted 3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles

  摘要：

  The condensation of cyclohexylidene(cyano)thioacetamides with aldehydes or of 2-acyl-1-(morpholin-4-yl)cycloalkenes with dithiomalonamide gave 1-alkyl(aryl)-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles. Reactions of the latter with various alkylating agents selectively produced the corresponding isoquinolin-3-yl sulfides or products of their subsequent Thorpe cyclization, thieno[2,3-c]isoquinolines.

  DOI：

  10.1134/s1070428012120081
• 作为产物：
  描述：

  2-cyano-2-cyclohexylidenethioacetamide 、 异丁醛 在 sodium 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以68%的产率得到1-isopropyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
  参考文献：
  名称：

  Synthesis and alkylation of 1-substituted 3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles

  摘要：

  The condensation of cyclohexylidene(cyano)thioacetamides with aldehydes or of 2-acyl-1-(morpholin-4-yl)cycloalkenes with dithiomalonamide gave 1-alkyl(aryl)-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles. Reactions of the latter with various alkylating agents selectively produced the corresponding isoquinolin-3-yl sulfides or products of their subsequent Thorpe cyclization, thieno[2,3-c]isoquinolines.

  DOI：

  10.1134/s1070428012120081

文献信息

• Synthesis and alkylation of 1-substituted 3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles
  作者：I. V. Dyachenko、M. V. Vovk

  DOI：10.1134/s1070428012120081

  日期：2012.12

  The condensation of cyclohexylidene(cyano)thioacetamides with aldehydes or of 2-acyl-1-(morpholin-4-yl)cycloalkenes with dithiomalonamide gave 1-alkyl(aryl)-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles. Reactions of the latter with various alkylating agents selectively produced the corresponding isoquinolin-3-yl sulfides or products of their subsequent Thorpe cyclization, thieno[2,3-c]isoquinolines.