1,6-cyclododecadiyne | 136237-61-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,6-cyclododecadiyne
• 英文别名: Cyclododeca-1,6-diyne
• CAS: 136237-61-1
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: IQWLQLQOUNBNDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,7-cyclododecanedione bissemicarbazone 在 selenium(IV) oxide 、 铜 作用下， 生成 1,7-环十二碳二炔 、 1,6-cyclododecadiyne
  参考文献：
  名称：

  Synthesis and properties of medium-sized (C9-C12) carbocyclic diacetylenes

  摘要：

  The syntheses of 1,5-cyclononadiyne (3), 1,5-cyclodecadiyne (4), 1,5-cycloundecadiyne (5), 1,6-cycloundecadiyne (6), 1,6-cyclododecadiyne (7), and 1,7-cyclododecadiyne (8) have been carried out. Diacetylenes 3 and 4 are prepared from 5-cyclononynone and 5-cyclodecynone, respectively. Compounds 5-8 are synthesized from cyclic diones by thermolysis of the corresponding bisselenadiazoles. The obtained cyclic diacetylenes are further characterized by their bis(hexacarbonyldicobalt) complexes. The geometrical parameters of 3-8 were calculated with force field and semiempirical methods. From the structural data, a correlation between the C-13 resonance of the sp-hybridized carbon atoms adjacent to the ethano bridge in 3-5 and the corresponding resonance of the symmetric dialkynes 1,5-cyclooctadiyne (1), 1,6-cyclodecadiyne (2), and 1,7-cyclododecadiyne (8) with the bending angle at this center can be verified. The PE spectra of 3-8 have been recorded, and an interpretation of the bands in the low-energy region is presented. It is found that the splitting of the PE bands that are assigned to the in-plane pi-MO's (pi-i) strongly depends on the size of the methylene bridge. In the case of a propano bridge (e.g., in 3, 6, and 7), the splitting between pi-i- and pi=i+ is relatively large. The splitting of the bands that are assigned to the out-of-plane pi-MO's (pi-o) decreases with increasing transannular distance.

  DOI：

  10.1021/ja00024a035

文献信息

• Synthesis and properties of medium-sized (C9-C12) carbocyclic diacetylenes
  作者：R. Gleiter、D. Kratz、W. Schaefer、V. Schehlmann

  DOI：10.1021/ja00024a035

  日期：1991.11

  The syntheses of 1,5-cyclononadiyne (3), 1,5-cyclodecadiyne (4), 1,5-cycloundecadiyne (5), 1,6-cycloundecadiyne (6), 1,6-cyclododecadiyne (7), and 1,7-cyclododecadiyne (8) have been carried out. Diacetylenes 3 and 4 are prepared from 5-cyclononynone and 5-cyclodecynone, respectively. Compounds 5-8 are synthesized from cyclic diones by thermolysis of the corresponding bisselenadiazoles. The obtained cyclic diacetylenes are further characterized by their bis(hexacarbonyldicobalt) complexes. The geometrical parameters of 3-8 were calculated with force field and semiempirical methods. From the structural data, a correlation between the C-13 resonance of the sp-hybridized carbon atoms adjacent to the ethano bridge in 3-5 and the corresponding resonance of the symmetric dialkynes 1,5-cyclooctadiyne (1), 1,6-cyclodecadiyne (2), and 1,7-cyclododecadiyne (8) with the bending angle at this center can be verified. The PE spectra of 3-8 have been recorded, and an interpretation of the bands in the low-energy region is presented. It is found that the splitting of the PE bands that are assigned to the in-plane pi-MO's (pi-i) strongly depends on the size of the methylene bridge. In the case of a propano bridge (e.g., in 3, 6, and 7), the splitting between pi-i- and pi=i+ is relatively large. The splitting of the bands that are assigned to the out-of-plane pi-MO's (pi-o) decreases with increasing transannular distance.