13,14-Diheptyl-7,9,11,16,18,20-hexathiaoctacyclo[13.9.0.02,12.03,10.04,8.05,22.017,24.019,23]tetracosa-1(15),2(12),3(10),4(8),5,13,17(24),19(23),21-nonaene | 1198158-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 13,14-Diheptyl-7,9,11,16,18,20-hexathiaoctacyclo[13.9.0.02,12.03,10.04,8.05,22.017,24.019,23]tetracosa-1(15),2(12),3(10),4(8),5,13,17(24),19(23),21-nonaene
• CAS: 1198158-91-6
• 化学式: C₃₂H₃₂S₆
• 分子量: 609.002
• InChiKey: ICMMCBUNQJNMMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,22-Dibromo-13,14-diheptyl-7,9,11,16,18,20-hexathiaheptacyclo[13.9.0.02,12.03,10.04,8.017,24.019,23]tetracosa-1(15),2(12),3(10),4(8),5,13,17(24),19(23),21-nonaene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以78%的产率得到13,14-Diheptyl-7,9,11,16,18,20-hexathiaoctacyclo[13.9.0.02,12.03,10.04,8.05,22.017,24.019,23]tetracosa-1(15),2(12),3(10),4(8),5,13,17(24),19(23),21-nonaene
  参考文献：
  名称：

  Intramolecular Cyclization of Thiophene-Based [7]Helicenes to Quasi-[8]Circulenes

  摘要：

  Intramolecular cyclization in a series of thiophene-based dibromo[7]helicenes (4-6) with different helix Structures is investigated by vacuum pyrolysis, tin- and palladium-mediated C-C bond forming reactions. The product With the cyclic structure of the annelated aromatic rings, which resembles [S]circulene devoid of an atom linkage, is referred to as quasi-[8]circulene. Vacuum pyrolysis of 4 gives insoluble, unidentified products, while 5 and 6 yield the corresponding quasi-[8]circulenes Under similar conditions. Thermogravimetry (TG) and differential scanning calorimetry (DSC) analyses for 4 indicate complex reaction pathways, while those for 5 and 6 show a single process corresponding to a loss of 1 equiv of Br-2 at about 330 degrees C. Pd-mediated reductive cyclization provides quasi-[8]circulenes for all three [7]helicenes, though only 4 gives a good isolated yield. Tributyltin hydride-mediated radical cyclization of 4-6 provides quasi-[8]circulenes In excellent yields, and it is practically insensitive to the helix Structure. Experimental and calculated UV-vis absorption spectra for quasi-[8]circulenes and [8]circulenes are reported. The results suggest that the lack of atom linkage in quasi-[8]circulene does not significantly affect properties and conformation, compared to those for the corresponding [8]circulenes.

  DOI：

  10.1021/jo902030u