3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarboxylic acid | 1392512-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarboxylic acid
• 英文别名: 6,13,20-Trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarboxylic acid；6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarboxylic acid
• CAS: 1392512-61-6
• 化学式: C₂₇H₂₄O₉
• 分子量: 492.482
• InChiKey: UUDDLKLXLHOOEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Triethyl 6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarboxylic acid
  参考文献：
  名称：

  Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and π-Conjugated Groups

  摘要：

  Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or pi-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C-3-triiodocyclotriveratrylene (CTV-I-3), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with pi-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I-3 to introduce novel functionalities into CTVs to keep exploring their potential applications.

  DOI：

  10.1021/jo301183b

文献信息

• Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and π-Conjugated Groups
  作者：Lisa Peyrard、Marie-Laurence Dumartin、Sabine Chierici、Sandra Pinet、Gediminas Jonusauskas、Pierre Meyrand、Isabelle Gosse

  DOI：10.1021/jo301183b

  日期：2012.8.17

  Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or pi-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C-3-triiodocyclotriveratrylene (CTV-I-3), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with pi-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I-3 to introduce novel functionalities into CTVs to keep exploring their potential applications.