triptycene-1,4,5,8-tetracarboxylic acid | 945681-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: triptycene-1,4,5,8-tetracarboxylic acid
• 英文别名: Pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-3,6,10,13-tetracarboxylic acid；pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-3,6,10,13-tetracarboxylic acid
• CAS: 945681-53-8
• 化学式: C₂₄H₁₄O₈
• 分子量: 430.37
• InChiKey: RPYKYCMYBSMWPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  triptycene-1,4,5,8-tetracarboxylic acid 在 lithium aluminium tetrahydride 、 正丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 Dimethyl 2-[[6,10,13-tris[[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]methyl]-3-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl]methylidene]-1,3-dithiole-4,5-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：

  1,4,5,8-tetramethylanthracene 在 potassium permanganate 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 吡啶 、 水 、 1,2-二氯乙烷 为溶剂， 反应 31.0h， 生成 triptycene-1,4,5,8-tetracarboxylic acid
  参考文献：
  名称：

  高度对称的三蝶烯四和六羧酸盐的合成

  摘要：

  已在标题化合物的合成中检验了两种替代方法，均从容易获得的四甲基蒽开始，并采用 Diels-Alder 加成作为关键反应步骤。

  DOI：

  10.1055/s-2007-966042

文献信息

• Tetrathiafulvalene-functionalized triptycenes: synthetic protocols and elucidation of intramolecular Coulomb repulsions in the oxidized species
  作者：Jiří Rybáček、Markéta Rybáčková、Martin Høj、Martin Bělohradský、Petr Holý、Kristine Kilså、Mogens Brøndsted Nielsen

  DOI：10.1016/j.tet.2007.06.020

  日期：2007.9

  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.
• Synthesis of Highly Symmetrical Triptycene Tetra- and Hexacarboxylates
  作者：Jiří Závada、Markéta Rybáčková、Martin Bělohradský、Petr Holý、Radek Pohl、Václav Dekoj

  DOI：10.1055/s-2007-966042

  日期：——

  Two alternative procedures, both starting from easily accessible- tetramethylanthracenes and employing the Diels-Alder addition as the key reaction step(s), have been examined in the synthesis of the title compounds.

  已在标题化合物的合成中检验了两种替代方法，均从容易获得的四甲基蒽开始，并采用 Diels-Alder 加成作为关键反应步骤。