9,10-dihexyloxy-3,6-diiodophenanthrene | 1269630-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,10-dihexyloxy-3,6-diiodophenanthrene
• 英文别名: 3,6-diiodo-9,10-bis(hexyloxy)phenanthrene；9,10-Dihexoxy-3,6-diiodophenanthrene；9,10-dihexoxy-3,6-diiodophenanthrene
• CAS: 1269630-98-9
• 化学式: C₂₆H₃₂I₂O₂
• 分子量: 630.348
• InChiKey: YLXBETGSQJQQGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  85.7-87.0 °C
• 沸点：
  615.0±50.0 °C(predicted)
• 密度：
  1.519±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.12
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((3-ethynylbicyclo[1.1.1]pent-1-yl)ethynyl)trimethylsilane 、 9,10-dihexyloxy-3,6-diiodophenanthrene 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3,6-bis((3-ethynylbicyclo[1.1.1]pentane-1-yl)ethynyl)-9,10-bis(hexyloxy)phenanthrene
  参考文献：
  名称：

  A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone

  摘要：

  A triangular macrocyclic molecule has been synthesized which consists of substituted phenanthrene vertices interconnected by 1,3-diethynylbicyclo[1.1.1]pentane sides. The molecule is the very first example of exploiting the bicyclopentane motif in the construction of a shape persistent macrocycle's backbone. It carries new features such as bulkiness, nonconjugated sigma-bonding, and a certain conformational flexibility due to its easy longitudinal rotation. We have used some of the features in order to rationalize the observed tendency of the compound to form films on various surfaces.

  DOI：

  10.1021/ol1031816
• 作为产物：
  描述：

  3,6-二溴-9,10-二(己氧基)菲 在 叔丁基锂 、 碘 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.67h， 以88%的产率得到9,10-dihexyloxy-3,6-diiodophenanthrene
  参考文献：
  名称：

  A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone

  摘要：

  A triangular macrocyclic molecule has been synthesized which consists of substituted phenanthrene vertices interconnected by 1,3-diethynylbicyclo[1.1.1]pentane sides. The molecule is the very first example of exploiting the bicyclopentane motif in the construction of a shape persistent macrocycle's backbone. It carries new features such as bulkiness, nonconjugated sigma-bonding, and a certain conformational flexibility due to its easy longitudinal rotation. We have used some of the features in order to rationalize the observed tendency of the compound to form films on various surfaces.

  DOI：

  10.1021/ol1031816

文献信息

• Synthesis and properties of π-conjugated donor–acceptor macrocycles derived from phenanthrylene building blocks
  作者：Bhimrao Vaijnath Phulwale、Sushil Kumar Mishra、Ctibor Mazal

  DOI：10.1016/j.tet.2018.05.025

  日期：2018.7

  intramolecular-charge-transfer (ICT) excited state was observed mainly in non-polar solvents. In more polar solvents, the excited states favor non-radiative relaxation. DFT calculated HOMO/LUMO energies of the macrocycles correlate well with spectroscopic and electrochemical data. In the series of substituted dibenzophenazine acceptors a good correlation with Hammett substituent constants σp– was found.

  合成了在其形状持久性完全共轭的核中结合了电子供体和电子受体亚基的菲撑乙炔大环。供体亚基由两个9，10-二烷氧基菲与1，2-乙叉基或2，5-亚噻吩基桥连接。受体是9，10-菲咯醌和二苯并喹喔啉和由其衍生的二苯并吩嗪。主要在非极性溶剂中观察到由分子内电荷转移（ICT）激发态引起的溶剂变色光致发光。在极性更大的溶剂中，激发态有利于非辐射弛豫。DFT计算得出的大环的HOMO / LUMO能量与光谱和电化学数据密切相关。在一系列取代的二苯并吩嗪受体中，与哈米特取代基常数σ具有良好的相关性p –被发现。
• 1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block
  作者：Jiří Kaleta、Marek Nečas、Ctibor Mazal

  DOI：10.1002/ejoc.201200351

  日期：2012.9

  that afford the corresponding dibromo and diiodo derivatives of DEBCP, which then successfully react with tert-C-cuprates derived from p- and m-dicarbadodecaboranes or bicyclopentanes. These umpolung reactions afforded a new class of molecular rods that combine carborane or bicyclo[1.1.1]pentane cages with ethynylene linkers. Many of the DEBCP derivatives were studied by single-crystal X-ray diffraction

  已发现 1,3-二乙炔基双环 [1.1.1] 戊烷 (DEBCP) 是一种有价值的分子构建块，主要用于合成延伸的刚性棒状分子。凭借其直接的线性几何形状，DEBCP 可用作更常用的 pi 共轭棒状构建块的非共轭替代品。将 DEBCP 引入更大结构的反应的例子是（1）DEBCP 乙炔锂与 TMSCl、CO2 和 Ph2PCl 等亲电试剂的反应，（2）Sonogashira-Hagihara 与芳基或杂芳基碘化物或溴化物的交叉偶联反应，以及（ 3) umpolung 反应提供相应的 DEBCP 的二溴和二碘衍生物，然后成功地与衍生自 p-和 m-dicarbadodecaboranes 或双环戊烷的叔-C-铜酸盐反应。这些 umpolung 反应提供了一类新的分子棒，将碳硼烷或双环 [1.1.1] 戊烷笼与乙炔连接体结合在一起。许多 DEBCP 衍生物通过单晶 X 射线衍射进行了研究。它们形成组织良好的分子转子阵列，DEBCP