1,4-dimethyltriptycene | 17417-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-dimethyltriptycene
• 英文别名: 2,5-Dimethyl-triptycen；3,6-dimethylpentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 17417-17-3
• 化学式: C₂₂H₁₈
• mdl: MFCD00408312
• 分子量: 282.385
• InChiKey: PCGUPPDXVDODQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1,4-dimethyltriptycene 在 potassium permanganate 、 硫酸 作用下， 以 吡啶 、 水 为溶剂， 反应 144.0h， 生成 diethyl triptycene-1,4-dicarboxylate
  参考文献：
  名称：

  Tetrathiafulvalene-functionalized triptycenes: synthetic protocols and elucidation of intramolecular Coulomb repulsions in the oxidized species

  摘要：

  A large selection of triptycenes functionalized with tetrathiafulvalene (TTF) units as well as triptycenes containing extended TTFs as a part of the triptycene core have been synthesized utilizing new triptycene di- and tetraaldehydes as well as bis-, tetrakis- and hexakis(bromomethyl) derivatives. The largest scaffold contains a total of 12 TTFs around the central triptycene core. From spectroelectro-chemical and chemical oxidation studies, we have elucidated the extent to which an increasing number of electrostatic interactions among oxidized TTF units exert an influence on the absorption characteristics. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.020
• 作为产物：
  描述：

  环己-1,3-二烯-5-炔 、 1,4-二甲基蒽 生成 1,4-dimethyltriptycene
  参考文献：
  名称：

  Barriers to rotation of methyl groups in methyltriptycenes

  摘要：

  DOI：

  10.1021/ja00372a023

文献信息

• New metal–organic frameworks from triptycene: structural diversity from bulky bridges
  作者：Angela K. Crane、Brian O. Patrick、Mark J. MacLachlan

  DOI：10.1039/c3dt00079f

  日期：——

  Four distinct triptycene-containing metal–organic frameworks, including three that are structural isomers, were synthesized and characterized. Structural isomerism was observed in the secondary building units of TMOF-2 giving rise to no fewer than three distinct [Zn4O]6+ clusters. Structural integrity upon guest solvent removal was confirmed using powder X-ray diffraction and thermogravimetric analysis, but gas adsorption experiments were conducted and revealed no appreciable surface area. Triptycenyl groups incorporated into MOFs appear to enhance structural diversity, but also crowd the pores of the MOF, reducing accessible surface area.

  合成并表征了四种不同的含三蝶烯的金属有机骨架，其中包括三种结构异构体。在 TMOF-2 的二级结构单元中观察到结构异构现象，产生不少于三个不同的 [Zn4O]6+ 簇。使用粉末 X 射线衍射和热重分析证实了客体溶剂去除后的结构完整性，但进行了气体吸附实验并显示没有明显的表面积。纳入 MOF 中的三蝶烯基似乎增强了结构多样性，但也堵塞了 MOF 的孔，减少了可及的表面积。
• A PHOTOLYTIC ONE-STEP SYNTHESIS AND STEREOCHEMISTRY OF 1,4-DIMETHYL-9-ARYLFLUORENES
  作者：Hiizu Iwamura

  DOI：10.1246/cl.1974.1205

  日期：1974.10.5

  Photolysis of 2,5-dimethyltriptycene (3) in methanol gives 1,4-dimethyl-9-(2-substituted phenyl)fluorenes 1 and 2 in 89 and 5 % yields, respectively. The results are interpreted in terms of the regioselective formation of intermediate carbene 4. The temperature dependent NMR study gives a rough estimate of ΔGc≠ value for restricted rotation around the C(9)-aryl bond in 2 as 19.4 kcal/mol (104°C).

  2,5-二甲基三苯乙烯 (3) 在甲醇中的光解得到 1,4-二甲基-9-（2-取代苯基）芴 1 和 2，产率分别为 89% 和 5%。结果根据中间体卡宾 4 的区域选择性形成进行解释。 温度相关的 NMR 研究给出了 2 中 C(9)-芳基键周围受限旋转的 ΔGc≠ 值的粗略估计为 19.4 kcal/mol (104° C）。
• Nuclear magnetic resonance spectra of some substituted benzotriptycenes: the effect of steric compression
  作者：Thomas H. Regan、Jerry Blair Miller

  DOI：10.1021/jo01284a033

  日期：1967.9
• Reactivity of benzyne toward anthracene systems
  作者：Bruce H. Klanderman、Thomas R. Criswell

  DOI：10.1021/jo01263a046

  日期：1969.11
• GUENZI, A.;JOHNSON, C. A.;COZZI, F.;MISLOW, K., J. AMER. CHEM. SOC., 1983, 105, N 6, 1438-1448
  作者：GUENZI, A.、JOHNSON, C. A.、COZZI, F.、MISLOW, K.

  DOI：——

  日期：——