2,7,12-triethynyl-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene | 1392512-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,7,12-triethynyl-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
• 英文别名: 5,12,19-Triethynyl-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-triethynyl-6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene
• CAS: 1392512-65-0
• 化学式: C₃₀H₂₄O₃
• 分子量: 432.519
• InChiKey: ZVTNKUJYHSIOEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,7,12-triethynyl-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene 、 叠氮苯 在 sodium L-ascorbate 、 copper(II) sulfate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以40%的产率得到1-phenyl-4-[3,8,13-trimethoxy-7,12-bis(1-phenyl-1H-1,2,3-triazol-4-yl)-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-yl]-1H-1,2,3-triazole
  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
• 作为产物：
  描述：

  (+/-)-2,7,12-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 2,7,12-triethynyl-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
  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

• Cyclotribenzylene alkynylgold(<scp>i</scp>) phosphine complexes: synthesis, chirality, and exchange of phosphine
  作者：Jing Zhang、Nathalie Zorn、Emmanuelle Leize-Wagner、Marion Jean、Nicolas Vanthuyne、Enrique Espinosa、Emmanuel Aubert、Bruno Vincent、Jean-Claude Chambron

  DOI：10.1039/d3dt04279k

  日期：2024.3.19

  allowed us to detect the complexes as proton adducts. The intensities of the signals were stronger when the phosphine was more electron-rich. This technique was also used to investigate the exchange of phosphine betweeen pairs of CTB complexes. The scrambling reaction was demonstrated by the higher intensity of the signals of the complexes subjected to the exchange of a single phosphine ligand by comparison

  合成了外消旋和对映体纯形式的两种不同的炔基取代的C 3对称环三亚苄基 (CTB)，并制备并表征了六种金 ( I ) 膦络合物（CTB 和膦的性质不同），特别是通过 NMR 光谱进行表征、DOSY、电子圆二色性 (ECD) 和电喷雾电离质谱 (ESI-MS)。它们的 ECD 模式取决于起始 CTB 的替换，并且与后者相比发生红移。 HCO 2 H 存在下的 ESI-MS 使我们能够将复合物检测为质子加合物。当磷化氢富含电子时，信号强度更强。该技术还用于研究 CTB 复合物对之间磷化氢的交换。与起始复合物的信号强度相比，经过单一膦配体交换的复合物的信号强度更高，证明了加扰反应。
• 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.