2-ethyl-1,2-dihydroanthracene | 126694-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-ethyl-1,2-dihydroanthracene
• CAS: 126694-96-0
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: ZDICECGKWUZNGK-UHFFFAOYSA-N

物化性质

• 沸点：
  340.3±17.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  溴乙烷 在 magnesium anthracene * 3 THF 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 9-ethyl-9,10-dihydroanthracene 、 9,10-diethyl-9,10-dihydroanthracene 、 乙基溴化镁 、 2-ethyl-1,2-dihydroanthracene
  参考文献：
  名称：

  Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg, Chemische Berichte, 1990, vol. 123, # 7, p. 1507 - 1515

  摘要：

  DOI：

文献信息

• Activation parameters for the competing electron transfer and SN2 pathways of the reaction of anthracene radical anion with cyclopropylmethyl bromide
  作者：Henrik Jensen、Heidi Skovbak Sørensen、Steen Uttrup Pedersen、Kim Daasbjerg

  DOI：10.1039/b203858g

  日期：——

  The reaction between the electrogenerated radical anion of anthracene and alkyl halides has been studied in the temperature interval of −50 to 40 °C in N,N-dimethylformamide in order to describe in detail the competition between the electron transfer (ET) and SN2 pathways. For cyclopropylmethyl bromide the competition can be quantified directly on the basis of an analysis of the distribution of ring-opened

  电生成之间的反应 自由基阴离子 的 蒽 在-50至40°C的温度区间内对卤代烷进行了研究。 N，N-二甲基甲酰胺为了详细描述电子转移（ET）和S N 2途径之间的竞争。为了环丙基甲基溴竞争可以基于对开环产品与闭环产品分布的分析直接量化。通常，尽管随着温度降低，S N 2途径变得更加重要，但发现ET途径占主导。当产物分析与反应总速率常数的测量结合时，可以提取两种机理的相关活化参数。如所期望的，由于在S N的过渡态中存在更强的键合相互作用，因此ΔH ‡ S N 2小于ΔH ‡ ET（高出7 kJ mol -1）。2.另一方面，由于较小的几何限制（ΔS ‡ ET - ΔS ‡ S N 2 = 37 J mol -1 K -1），熵得到了熵的支持，因此，这种效果远远超过了抵消效果。S N 2机制导致在9位的取代蒽而对于ET机制，它发生在1、2和9这三个位置。在这三个位置中，产品的总体分布在很大程度
• Competitive Electron Transfer and SN2 Reactions of Aromatic Radical Anions with Alkyl Halides and Methanesulfonates.
  作者：Heidi Skovbak Sørensen、Kim Daasbjerg、Lennart Eberson、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0051

  日期：——

  The competition between electron transfer and S(N)2 processes in the reaction between a number of radical anions of aromatic compounds such as anthracene, pyrene, (E)-stilbene, m-tolunitrile and p-tolunitrile and different substrates such as the methyl, ethyl, butyl, 2-butyl, neopentyl and I-adamantyl halides as well as methyl, ethyl, butyl and 2-butyl methanesulfonates has been investigated in N,N-dimethylformamide. By using the reaction of the radical anions with the appropriate alkyldimethylsulfonium iodide or trialkylsulfonium iodide as model for an electron transfer process the reaction mechanism could be characterized by electrochemical means in many of the cases listed. The presence of an S(N)2 component is found to be related not only to the steric requirements at the substrate but also to the magnitude of the driving force for the electron transfer process. Ln general, the higher the standard potential of the aromatic compound is or the poorer the substrate is as electron acceptor, the more important the S(N)2 mechanism becomes. An analysis of the substitution products obtained in the reaction between anthracene radical anion and the different substrates shows a considerable rise in the yield of the 9-alkyl-9,10-dihydroanthracene isomer as the magnitude of the S(N)2 component increases.