α-methyl-p-xylylene | 1026730-76-6

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 醌二甲烷类
• 英文名称: α-methyl-p-xylylene
• 英文别名: 3-Ethylidene-6-methylidenecyclohexa-1,4-diene
• CAS: 1026730-76-6
• 化学式: C₉H₁₀
• 分子量: 118.178
• InChiKey: WSBCXIVCVYIHCM-UHFFFAOYSA-N

物化性质

• 沸点：
  182.1±7.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  α-methyl-p-xylylene 以 氘代乙腈 为溶剂， 生成 2,8-Dimethyl-tricyclo[8.2.2.2^4,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaene 、 2,3-Dimethyl-tricyclo[8.2.2.2^4,7]hexadeca-1(13),4,6,10(14),11,15-hexaene 、 2,8,14-Trimethyltetracyclo[14.2.2.24,7.210,13]tetracosa-1(19),4,6,10(22),11,13(21),16(20),17,23-nonaene 、 2,3,9-Trimethyltetracyclo[14.2.2.24,7.210,13]tetracosa-1(19),4,6,10(22),11,13(21),16(20),17,23-nonaene
  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
• 作为产物：
  描述：

  (4-羟基苄基)三甲基硅烷 在 吡啶 、 四丁基氟化铵 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氘代乙腈 为溶剂， 反应 2.75h， 生成 α-methyl-p-xylylene
  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