4,8-dimethyl<2.2>paracyclophane | 107171-17-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,8-dimethyl<2.2>paracyclophane
• 英文别名: 4,8-dimethyl[2.2]paracyclophane；5,16-Dimethyltricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
• CAS: 107171-17-5
• 化学式: C₁₈H₂₀
• 分子量: 236.357
• InChiKey: GVDVBFYONQEEES-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C(Solvent: Benzene ; Hexane)
• 沸点：
  354.6±37.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3,4,5-三甲基苯胺 在 吡啶 、 盐酸 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 硫酸 、 四丁基氟化铵 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 氘代乙腈 、 正戊烷 为溶剂， 反应 0.17h， 生成 4,8-dimethyl<2.2>paracyclophane
  参考文献：
  名称：

  Room Temperature Observation of p-Xylylenes by ¹H NMR and Evidence for Diradical Intermediates in Their Oligomerization

  摘要：

  p-Quinodimethanes (p-QDMs) are reactive molecules that have been invoked as transient intermediates in a number of reactions. Dilute solutions of benzene-based p-QDMs, p-xylylene (1), a-methyl-p-xylylene (10), and 2,5-dimethyl-p-xylylene (11) can be prepared by fluoride-induced elimination of trimethylsilyl acetate from the appropriate precursor. It has been found that these solutions are stable enough to allow these reactive p-QDMs to be observed by H-1 NMR spectroscopy at room temperature. For the first time, the 13 C NMR spectrum of p-QDM 1 was observed. After several hours at room temperature, these p-QDMs form dimers, trimers, and insoluble oligomers. Formation of trimers provides evidence that p-QDMs 1, 10, and 11 dimerize by a stepwise mechanism involving dimeric diradicals as intermediates.

  DOI：

  10.1021/jo0516279

文献信息

• Photodimerization of benzenes in strained dihetera[3.3]metacyclophanes
  作者：Hiroyuki Higuchi、Eiji Kobayashi、Yoshiteru Sakata、Soichi Misumi

  DOI：10.1016/s0040-4020(01)87590-6

  日期：——
• HIGUCHI, HIROYUKI;KOBAYASHI, EIJI;SAKATA, YOSHITERU;MISUMI, SOICHI, TETRAHEDRON, 1986, 42, N 6, 1731-1739
  作者：HIGUCHI, HIROYUKI、KOBAYASHI, EIJI、SAKATA, YOSHITERU、MISUMI, SOICHI

  DOI：——

  日期：——
• Room Temperature Observation of <i>p-</i>Xylylenes by ¹H NMR and Evidence for Diradical Intermediates in Their Oligomerization
  作者：Walter S. Trahanovsky、Steven P. Lorimor

  DOI：10.1021/jo0516279

  日期：2006.3.1

  p-Quinodimethanes (p-QDMs) are reactive molecules that have been invoked as transient intermediates in a number of reactions. Dilute solutions of benzene-based p-QDMs, p-xylylene (1), a-methyl-p-xylylene (10), and 2,5-dimethyl-p-xylylene (11) can be prepared by fluoride-induced elimination of trimethylsilyl acetate from the appropriate precursor. It has been found that these solutions are stable enough to allow these reactive p-QDMs to be observed by H-1 NMR spectroscopy at room temperature. For the first time, the 13 C NMR spectrum of p-QDM 1 was observed. After several hours at room temperature, these p-QDMs form dimers, trimers, and insoluble oligomers. Formation of trimers provides evidence that p-QDMs 1, 10, and 11 dimerize by a stepwise mechanism involving dimeric diradicals as intermediates.