2,3,4,5,6,7,8,10,11,12,13,14,15,16-hexadecahydro-4,12-bis(alkynyl)-1H,9H-dicyclodeca[b,d]thiophene | 675126-51-9

• 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: 2,3,4,5,6,7,8,10,11,12,13,14,15,16-hexadecahydro-4,12-bis(alkynyl)-1H,9H-dicyclodeca[b,d]thiophene
• 英文别名: 1,2,3,6,7,8,9,10,11,14,15,16-dodecahydro-4,5,12,13-tetradehydro-1H,9H-dicyclodeca[b,d] thiophene；Agn-PC-0LP4CE；12-thiatricyclo[11.8.0.02,11]henicosa-1(13),2(11)-dien-6,17-diyne
• CAS: 675126-51-9
• 化学式: C₂₀H₂₄S
• 分子量: 296.477
• InChiKey: FJUSRJRBQPJBBH-UHFFFAOYSA-N

物化性质

• 沸点：
  452.5±45.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  decamethylrhenocene 、 2,3,4,5,6,7,8,10,11,12,13,14,15,16-hexadecahydro-4,12-bis(alkynyl)-1H,9H-dicyclodeca[b,d]thiophene 以 均三甲苯 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  Synthesis and Properties of a Superphane with One Thiophene and One CpCo-Stabilized Cyclobutadiene Ring

  摘要：

  A superphane consisting of one thiophene ring and one CpCo-stabilized cyclobutadiene ring, 8, was prepared in an eight-step synthesis from 5-cyclodecynol protected with tert-butyldimethylsilyl, 13. The first key step in this sequence was the reaction of 13 with zirconocene and subsequently with S2Cl2 to yield the tricyclic thiophene derivative 12. The second key step was the ring closure of 11 with CpCo(COD) to give 8. X-ray structural investigations of 11 and 8 confirmed the structural assignments. Evidence for the close proximity of the CpCo-stabilized cyclobutadiene and the thiophene rings is also given by the electronic absorption spectrum of 8 and the oxidation potential (-0.07 V).

  DOI：

  10.1021/om030619k

文献信息

• Transannular Interactions in Mixed Superphanes with One Thiophene and One CpCo-Stabilized Cyclobutadiene Ring:  Syntheses, Structures, and Electrochemistry
  作者：Silke Gath、Rolf Gleiter、Frank Rominger、Christian Bleiholder

  DOI：10.1021/om0608206

  日期：2007.1.1

  Superphanes consisting of one thiophene ring and various substituted RCo-stabilized cyclobutadiene (CBD) rings (R = Cp, C5H4(CH3), C-5(CH3)(5), C5H4(Si(CH3)(3)), C5H4(COCH3), 8-12) and one superphane with one thiophene ring and one CpCo-stabilized cyclopentadienone ring (13) were synthesized. The starting point was a tricyclic diyne with a central thiophene ring and two condensed 4-cyclodecynes, 19. Heating of 19 with RCo(COD) yielded 8-12, whereas the heating of 19 with CpCo(CO)(2) gave 13. X-ray structural investigation of 8-13 afforded the geometrical parameters in the solid state. Cyclic voltammetry showed a strong interaction between the thiophene ring and the CpCo-stabilized cyclobutadiene part. This interaction was substantiated by comparison between the CV data of 8-12 and model systems containing only the CpCo(CBD) part.