5,14-disopropylidenecyclotetradeca-1,3,6,12-tetrayne | 7234-05-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5,14-disopropylidenecyclotetradeca-1,3,6,12-tetrayne
• 英文别名: 5,14-Di(propan-2-ylidene)cyclotetradeca-1,3,6,12-tetrayne
• CAS: 7234-05-1
• 化学式: C₂₀H₂₀
• 分子量: 260.379
• InChiKey: CBFZNQDKTDOPCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3,12-Diethynyl-2,13-dimethyl-tetradeca-2,12-diene-4,10-diyne 在 copper(l) iodide 、 四甲基乙二胺 、 氧气 作用下， 以 二氯甲烷 为溶剂， 生成 5,14-disopropylidenecyclotetradeca-1,3,6,12-tetrayne
  参考文献：
  名称：

  Cyclic alkynes–electronic behaviour as a function of ring strain

  摘要：

  随着环应变和平面度的增加，对一系列交叉共轭烯二炔大环进行的紫外/可见光谱分析表明，尽管 13C NMR 光谱显示亚烷基碳原子发生了明显的再杂化，但这对大环的电子吸收几乎没有影响。

  DOI：

  10.1039/a900910h

文献信息

• Structural, Vibrational, and Electronic Characteristics of Enyne Macrocycles as a Function of Ring Strain
  作者：Sara Eisler、Robert McDonald、Glen R. Loppnow、Rik R. Tykwinski

  DOI：10.1021/ja000617g

  日期：2000.7.26

  The cross-conjugated macrocycles 8a-e and acyclic model compound 12 have been synthesized and thoroughly analyzed by H-1 and C-13 NMR, UV, IR, and Raman spectroscopies, and by X-ray crystallography. The increasing ring strain and resultant changes in the double and triple bond orders are clearly detailed in the Raman and C-13 NMR spectra, as well as in the X-ray structures. Correlations between C-13 NMR shifts, bond angles, and Raman frequencies are essentially linear for the butadiynyl and olefinic moieties. The most highly strained system, 8a, displays interior alkylidene bond angles that are reduced to 108 degrees and alkyne angles reduced to as little as 155 degrees. The electronic absorption spectrum of 8a shows evidence of through-space homoconjugation that is manifested as a bathochromic shift of the absorption band arising from the in-plane pi-system. The absorption bands from the out-of-plane pi-electron systems of the more strained cycles 8a and 8b show slight bathochromic shifts as compared with the less strained systems 8c-e and acyclic 12, Ring strain, however, has a surprisingly small effect on the electronic absorption energies of these macrocycles.