9-(4-溴丁基)蒽 | 155827-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-(4-溴丁基)蒽
• 英文名称: 4-(9-anthracenyl)butyl bromide
• 英文别名: 9-(4-bromobutyl)anthracene；1-bromo-4-(9-anthracenyl)butane
• CAS: 155827-12-6
• 化学式: C₁₈H₁₇Br
• 分子量: 313.237
• InChiKey: VKDWNMPLUHSKKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  9-(4-溴丁基)蒽 生成 4-(9-anthracenyl)butyl amine
  参考文献：
  名称：

  Gaining control over molecular threading: benefits of second coordination sites and aqueous–organic interfaces in rotaxane synthesis

  摘要：

  Rotaxane的合成由于轴体试剂上有两个功能团而得以促进；与均相相相比，在混合的水-有机相中反应，rotaxane的产率也显著提高；这种好处可能与界面反应有关。

  DOI：

  10.1039/c39950001289
• 作为产物：
  描述：

  1,4-二溴丁烷 、 9-溴蒽 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以42%的产率得到9-(4-溴丁基)蒽
  参考文献：
  名称：

  Microwave accelerated facile synthesis of fused polynuclear hydrocarbons in dry media by intramolecular Friedel–Crafts alkylation

  摘要：

  在微波辐照下，相应的 1-bromo-4-arylbutanes 在干燥介质中通过分子内 FriedelâCrafts 烷基化反应，以快速、简单、高产率和区域特异性的方法合成了融合的多核四氢壬烷。分子建模研究表明，观察到的反应活性是一种协同机制的结果。

  DOI：

  10.1039/b311750m

文献信息

• Gaining control over molecular threading: benefits of second coordination sites and aqueous–organic interfaces in rotaxane synthesis
  作者：Alexander G. Kolchinski、Daryle H. Busch、Nathaniel W. Alcock

  DOI：10.1039/c39950001289

  日期：——

  Rotaxane synthesis is facilitated by the presence of two functional groups on the axle reagent; the yield of rotaxane is also substantially improved by reaction in a mixed aqueous–organic phase, compared to a homogeneous phase; the benefit may be associated with reaction at the interface.

  Rotaxane的合成由于轴体试剂上有两个功能团而得以促进；与均相相相比，在混合的水-有机相中反应，rotaxane的产率也显著提高；这种好处可能与界面反应有关。
• Donor−Acceptor Interaction and Photochemistry of Polymethylene-Linked Bichromophores in Solution
  作者：Song-lei Zhang、Matthew J. Lang、Steven Goodman、Christopher Durnell、Vlastimil Fidlar、Graham R. Fleming、Nien-chu C. Yang

  DOI：10.1021/ja9523698

  日期：1996.1.1

  The ground-state and the excited-state spectroscopic properties of four series of polymethylene-linked anthracene-dialkylaniline bichromophores were compared as a probe to the relationship between energetics and distance in photoinduced electron transfer (PET). The results demonstrate that, when the energy level of the charge transfer (CT) stale is lowered below that of the localized excited state by appropriate substituents, there is a strong electron-donor-acceptor (EDA) interaction in the ground state which is absent in other bichromophores. Absorption and fluorescence excitation studies revealed that there is an unusually strong EDA interaction in the ground state of A-2 which is absent in other members in the A series. When A-2 is excited directly into this EDA absorption, it exhibits two CT emissions, one at 490 nm and the other at 605 nm. The quantum yield (tau(f)) and the lifetime (Phi(f)) of the two emissions are dependent on the viscosity of the alkane solvent. The Phi(f) and the tau(f) of the 490 nm emission increased when the solvent viscosity tvas increased; however, those of the 605 nm emission remained essentially unchanged. The risetime of the 605 nm emission is 420 ps, but that of the 490 nm emission is instrument-function limiting. The results suggest that the two CT emissions may be derived from the two different conformations of the CT state. The 490 nm emission may be derived from the trans conformer of A-2, which is the major conformer at equilibrium. The EDA interaction in the trans conformer of A-2 may be treated as a type of through-sigma-bond interaction via the spacer between the n orbital of the anilino nitrogen and the pi orbital of the anthryl group. The direct excitation of A-2 from its EDA ground state to the CT state indicates that PET may occur in a sigma-linked bichromophoric system upon light absorption, thus reaching the limiting rate of a photochemical process.
• Microwave accelerated facile synthesis of fused polynuclear hydrocarbons in dry media by intramolecular Friedel–Crafts alkylation
  作者：Vanya B. Kurteva、António Gil Santos、Carlos A. M. Afonso

  DOI：10.1039/b311750m

  日期：——

  Fused polynuclear tetrahydro arenes are synthesised in a fast, simple, high yielding and regiospecific procedure by an intramolecular Friedel–Crafts alkylation in dry media under microwave irradiation of the corresponding 1-bromo-4-arylbutanes immobilised on silica. The observed reactivity is rationalised by molecular modelling studies which suggest the occurence of a concerted mechanism.

  在微波辐照下，相应的 1-bromo-4-arylbutanes 在干燥介质中通过分子内 FriedelâCrafts 烷基化反应，以快速、简单、高产率和区域特异性的方法合成了融合的多核四氢壬烷。分子建模研究表明，观察到的反应活性是一种协同机制的结果。
• Afonso, Carlos A. M.; Farinha, Journal of Chemical Research - Part S, 2002, # 11, p. 584 - 586
  作者：Afonso, Carlos A. M.、Farinha

  DOI：——

  日期：——