1-phenyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile | 94833-28-0

• 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-phenyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
• 英文别名: 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile；1-phenyl-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolinethione；1-phenyl-3-sulfanylidene-5,6,7,8-tetrahydro-2H-isoquinoline-4-carbonitrile
• CAS: 94833-28-0
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: STUSPCMHZXZZGE-UHFFFAOYSA-N

物化性质

• 沸点：
  471.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-溴环己酮 、 1-phenyl-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， 以67%的产率得到3-(2-oxocyclohexylthio)-1-phenyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile
  参考文献：
  名称：

  Cyanoselenoacetamide in a new synthesis of propane-bis(thioamide), the promising reagent for heterocyclizations

  摘要：

  Cyanoselenoacetamide reacts with hydrogen sulfide to form propane-bis(thioamide), which can be used to produce thiazoles (the Hantzsch synthesis) and 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile. From the latter compound, 2-alkylsulfanyl-1-phenyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles and 1-amino-N-(4-bromophenyl)-5-phenyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamide can be prepared.

  DOI：

  10.1134/s1070363213090168
• 作为产物：
  描述：

  2-cyano-2-cyclohexylidenethioacetamide 、 苯甲醛 在 sodium 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以69%的产率得到1-phenyl-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

• Sharanin, Yu. K.; Shestopalov, A. M.; Promonenkov, V. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1402 - 1415
  作者：Sharanin, Yu. K.、Shestopalov, A. M.、Promonenkov, V. K.、Rodinovskaya, L. A.

  DOI：——

  日期：——
• LEISTNER, SIEGFRIED;WAGNER, GUNTHER;STROHSCHEIDT, THOMAS;VIEWEG, HELMUT;G+
  作者：LEISTNER, SIEGFRIED、WAGNER, GUNTHER、STROHSCHEIDT, THOMAS、VIEWEG, HELMUT、G+

  DOI：——

  日期：——
• 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.
• Cyanoselenoacetamide in a new synthesis of propane-bis(thioamide), the promising reagent for heterocyclizations
  作者：I. V. Dyachenko、M. V. Vovk

  DOI：10.1134/s1070363213090168

  日期：2013.9

  Cyanoselenoacetamide reacts with hydrogen sulfide to form propane-bis(thioamide), which can be used to produce thiazoles (the Hantzsch synthesis) and 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile. From the latter compound, 2-alkylsulfanyl-1-phenyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles and 1-amino-N-(4-bromophenyl)-5-phenyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamide can be prepared.