1,1-di(2-thiocyanatoethyl)cyclohexane | 1070768-57-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,1-di(2-thiocyanatoethyl)cyclohexane
• 英文别名: 2-[1-(2-Thiocyanatoethyl)cyclohexyl]ethyl thiocyanate
• CAS: 1070768-57-8
• 化学式: C₁₂H₁₈N₂S₂
• 分子量: 254.42
• InChiKey: IBRGOIDSLKBMBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-di(2-thiocyanatoethyl)cyclohexane 、 1,4-二乙炔基苯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以0.4%的产率得到4,10,16,22,28,34-hexathia-1(1,4),13(1,4),25(1,4),37(1,4)-tribenzenacyclohexatriaconta-2,11,14,23,26,35-hexaynophane
  参考文献：
  名称：

  Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

  摘要：

  By means of four- and six-component cyclization reaction various cyclophanes were synthesized. The components were the di(lithium) salts of 1,4-di(ethynyl)benzene (11), 4,4'-di(ethynyl)biphenyl (13), 1,4-di(ethynyl)-2,5-di(n-hexyl)benzene (18), and 1,4-di(ethynyl)-2,5-di(n-propyl)benzene (19). These building blocks were reacted with alpha,omega-dithiocyanato-n-alkanes and alpha,omega-diselenocyanato-n-alkanes with n = 3-6. In the case of 10 also 1,1'-di(2-thiocyanatoethyl)cyclohexane (24) was reacted to afford a cyclophane comprising three subunits of 11. From most of the resulting macrocyclic cyclophanes (4(n) (n = 3, 5), 5, 6, 7(n), 8(n) (n = 3-6), 9(n) (n = 3, 5), and 10), we were able to grow single crystals. The X-ray analysis of 4(3), 7(3), 8(3), 8(4), 6, 7(5), and 8(5) revealed close contacts between the chalcogen atoms. These chalcogen-chalcogen interactions impose a ribbon-shape arrangement of molecules in 4(3) and a mutual crossing of two perdendicular planes built of 8(4) molecules. For 4(3) we found a close contact (3.28 angstrom) between the pi planes of two neighboring C6H4 rings of different molecules, whereas in 8(4) such a close contact (3.74 angstrom) was due to an intermolecular interaction. Tubular stacking of the macrocyclic rings was found for 7(5) and 8(5) caused by a ladder-type intermolecular chalcogen-chalcogen interaction.

  DOI：

  10.1021/jo801378p
• 作为产物：
  描述：

  1,1-di(2-methanesulfonyloxyethyl)cyclohexane 、 potassium thioacyanate 以 丙酮 为溶剂， 反应 14.0h， 以81%的产率得到1,1-di(2-thiocyanatoethyl)cyclohexane
  参考文献：
  名称：

  Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

  摘要：

  By means of four- and six-component cyclization reaction various cyclophanes were synthesized. The components were the di(lithium) salts of 1,4-di(ethynyl)benzene (11), 4,4'-di(ethynyl)biphenyl (13), 1,4-di(ethynyl)-2,5-di(n-hexyl)benzene (18), and 1,4-di(ethynyl)-2,5-di(n-propyl)benzene (19). These building blocks were reacted with alpha,omega-dithiocyanato-n-alkanes and alpha,omega-diselenocyanato-n-alkanes with n = 3-6. In the case of 10 also 1,1'-di(2-thiocyanatoethyl)cyclohexane (24) was reacted to afford a cyclophane comprising three subunits of 11. From most of the resulting macrocyclic cyclophanes (4(n) (n = 3, 5), 5, 6, 7(n), 8(n) (n = 3-6), 9(n) (n = 3, 5), and 10), we were able to grow single crystals. The X-ray analysis of 4(3), 7(3), 8(3), 8(4), 6, 7(5), and 8(5) revealed close contacts between the chalcogen atoms. These chalcogen-chalcogen interactions impose a ribbon-shape arrangement of molecules in 4(3) and a mutual crossing of two perdendicular planes built of 8(4) molecules. For 4(3) we found a close contact (3.28 angstrom) between the pi planes of two neighboring C6H4 rings of different molecules, whereas in 8(4) such a close contact (3.74 angstrom) was due to an intermolecular interaction. Tubular stacking of the macrocyclic rings was found for 7(5) and 8(5) caused by a ladder-type intermolecular chalcogen-chalcogen interaction.

  DOI：

  10.1021/jo801378p