7-甲基二环[4.2.0]辛-1,3,5-三烯 | 55337-80-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 7-甲基二环[4.2.0]辛-1,3,5-三烯
• 英文名称: α-Methylbenzocyclobuten
• 英文别名: 1-methyl-2-benzocyclobutene；3-Methylbenzocyclobutene；1,2-dihydro-1-methylbenzocyclobutene；7-methylbicyclo[4.2.0]octa-1,3,5-triene；1-Methyl-benzocyclobuten；1-methylcyclobutabenzene
• CAS: 55337-80-9
• 化学式: C₉H₁₀
• 分子量: 118.178
• InChiKey: DIIIHASDQIQOFX-UHFFFAOYSA-N

物化性质

• 沸点：
  85-105 °C(Press: 105 Torr)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  7-甲基二环[4.2.0]辛-1,3,5-三烯 生成 2-甲基苯乙烯
  参考文献：
  名称：

  苯并环丁烯热解路径的动力学研究

  摘要：

  描述了一种模拟闪蒸真空热解条件的简单气流反应器，该反应器可产生单分子气相反应的近似速率值，并已用于比较和优化导致苯并环丁烯的热解消除反应。

  DOI：

  10.1016/s0040-4039(00)88652-9
• 作为产物：
  描述：

  邻二氯苄 在 dilithium tetrachlorocuprate 、 magnesium 作用下， 647.0 ℃ 、10.67 Pa 条件下， 生成 7-甲基二环[4.2.0]辛-1,3,5-三烯
  参考文献：
  名称：

  通过快速真空热解形成取代的苯并环丁烯

  摘要：

  在关键步骤中，通过涉及热解1,4-消除HCl的反应顺序，由2-甲基苯甲醛以高收率获得在四元环中带有取代基的苯环丁烯。

  DOI：

  10.1016/s0040-4039(00)88653-0

文献信息

• The addition of benzocyclobutenylidene to benzene
  作者：Margaret A. O'Leary、Geoffrey W. Richardson、Dieter Wege

  DOI：10.1016/s0040-4020(01)97702-6

  日期：1981.1

  trans-10-methyl-9a, 10-dihydrobenz[α]azulene 3, respectively. A mechanism involving initially the addition of the carbene benzocyclobutenylidene, or its 2-Me derivative, to the benzene ring is postulated. A proposed intermediate in the reaction, spiro [benzocyclobutene 1,7' cyclohepta-1',3',5'-triene] 12 has been synthesised, and shown to give rise to 4 under the reaction conditions. The rate of rearrangement

  苯并环丁烯酮甲苯磺酸and和2-甲基苯并环丁酮甲苯磺酸the的钠盐在苯中的热分解分别得到9a，10-二氢苯并[α] azulene 4和反式-10-甲基-9a ，10-二氢苯并[α] azulene 3。推测最初涉及将卡宾苯并环丁烯基或其2- Me衍生物加至苯环的机理。反应中所建议的中间体螺[苯并环丁烯1,7'环庚-1'，3'，5'-三烯] 12已合成，显示在反应条件下可生成4。测量了12→4的重排速率，并确定了活化能：Ea＝ 125.9±0.8KJmol -1，A ＝ 1.38×10 14 sec -1。重排的机理必须涉及12的苯并环丁烯部分的开环以产生邻二甲苯中间体，该中间体被假定具有相当大的双自由基特性。在71.8°时，此开环速度比母体苯并环丁烯分子的开环速度快2.7×10 6倍。还研究了2-（7'-环庚-1'，3'，5'三烯基）苯甲醛甲苯磺酰the的钠盐的分解，结果表明生成4a，10-二氢苯并[α]
• Photolysis and flash thermolysis of some 1,3-dihydrobenzo[c]thiophen 2,2-dioxides
  作者：Tony Durst、Michael Lancaster、David J. H. Smith

  DOI：10.1039/p19810001846

  日期：——

  The thermolysis and photolysis of the title compounds (7) have been studied. Benzocyclobutenes (8) are the major products at lower temperatures whereas alkenes (9), derived from a [1,5] hydride shift, predominate at higher temperatures and on photolysis.

  已经研究了标题化合物（7）的热解和光解。苯并环丁烯（8）是较低温度下的主要产物，而衍生自[1,5]氢化物转移的烯烃（9）在较高温度和光解作用下占主导地位。
• Absorption spectra and photochemical rearrangements in phenylalkene cations in solid argon
  作者：Lester Andrews、James A. Harvey、Benuel J. Kelsall、Donald C. Duffey

  DOI：10.1021/ja00411a026

  日期：1981.10
• Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene
  作者：Wolfgang Kirmse、Wolfgang Konrad、Dirk Schnitzler

  DOI：10.1021/jo00093a014

  日期：1994.7

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).
• Bubb,W.A.; Sternhell,S., Australian Journal of Chemistry, 1976, vol. 29, p. 1685 - 1697
  作者：Bubb,W.A.、Sternhell,S.

  DOI：——

  日期：——