2-(三甲基甲硅烷基)苯并环丁烯基-1甲磺酸酯 | 126543-57-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 2-(三甲基甲硅烷基)苯并环丁烯基-1甲磺酸酯
• 英文名称: 2-(trimethylsilyl)benzocyclobutenyl-1 mesylate
• 英文别名: (8-Trimethylsilyl-7-bicyclo[4.2.0]octa-1,3,5-trienyl) methanesulfonate
• CAS: 126543-57-5；126543-58-6
• 化学式: C₁₂H₁₈O₃SSi
• 分子量: 270.425
• InChiKey: YDZUVDASZOCRQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(三甲基甲硅烷基)苯并环丁烯基-1甲磺酸酯 在 cesium fluoride 作用下， 以 氘代乙腈 为溶剂， 生成 6a,10b-dihydrobenzobiphenylene
  参考文献：
  名称：

  On the Mechanism of the Dimerization of Benzocyclobutadiene

  摘要：

  The dimerization of benzocyclobutadiene (1), generated by the fluoride ion-induced elimination of trimethylsilyl mesylate from 2-(trimethylsilyl)benzocyclobutenyl-1 mesylate (5), was carefully studied by flow NMR spectroscopy. Only formation of the final dimer, 6a,10b-dihydrobenzo[a]-biphenylene (2), was observed; no evidence for the formation of transient intermediates was obtained. Benzocyclobutadiene with a deuterium atom on position 1, l-dl, was prepared and allowed to dimerize. It is shown by several NMR spectroscopic techniques that l-dl dimerizes to produce six dideuterated isotopomers. It is proposed that the deuterium distribution is explained by a dimerization mechanism involving the formation of [4 + 2] dimer 3 followed by opening of 3 to form dibenzo[a,d]cyclooctatetraene (6) which closes to final dimer 2.

  DOI：

  10.1021/jo960975v

文献信息

• Observation of benzocyclobutadiene by flow nuclear magnetic resonance
  作者：Walter S. Trahanovsky、D. R. Fischer

  DOI：10.1021/ja00168a059

  日期：1990.6

  Benzocyclobutadiene (1) is a key molecule in the understanding of the aromaticity and antiaromaticity of cyclic delocalized pi}-electron systems. The high reactivity of 1 has made it difficult to study, but it has been isolated in an Ar matrix at 20 K, and its IR, UV-visible, and photoelectron spectra have been obtained. In this communication we report the sup 1}H NMR spectrum of 1 obtained by the

  苯并环丁二烯 (1) 是理解环状离域 pi} 电子系统的芳香性和反芳香性的关键分子。1 的高反应性使其难以研究，但它已在 20 K 的 Ar 基质中分离，并已获得其红外、紫外-可见光和光电子光谱。在本次通讯中，我们报告了通过流动核磁共振技术获得的 1 的 sup 1}H NMR 谱。