4,10,16,22-tetrathia-1²,1⁵,13²,13⁵-tetra(n-hexyl)-1(1,4),13(1,4)-dibenzenacyclotetracosa-2,11,14,23-tetraynophane | 1070768-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4,10,16,22-tetrathia-1²,1⁵,13²,13⁵-tetra(n-hexyl)-1(1,4),13(1,4)-dibenzenacyclotetracosa-2,11,14,23-tetraynophane
• 英文别名: 14,29,31,33-Tetrahexyl-4,10,19,25-tetrathiatricyclo[26.2.2.213,16]tetratriaconta-1(30),13(34),14,16(33),28,31-hexaen-2,11,17,26-tetrayne
• CAS: 1070768-54-5
• 化学式: C₅₄H₇₆S₄
• 分子量: 853.461
• InChiKey: KSUQAIUUKFUAEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.8
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-dithiocyanatopentane 、 苯,1,4-二乙炔基-2,5-二己基- 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 以8%的产率得到4,10,16,22-tetrathia-1²,1⁵,13²,13⁵-tetra(n-hexyl)-1(1,4),13(1,4)-dibenzenacyclotetracosa-2,11,14,23-tetraynophane
  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