10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarbonitrile | 1392512-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarbonitrile
• 英文别名: 3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarbonitrile；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-tricarbonitrile；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-tricarbonitrile
• CAS: 1392512-63-8
• 化学式: C₂₇H₂₁N₃O₃
• 分子量: 435.482
• InChiKey: VEGJFYCTEFNTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pt(1,3-bis(diphenylphosphino)propane)(trifluoromethanesulfonate)₂ 、 10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarbonitrile 以 二氯甲烷-D2 为溶剂， 生成
  参考文献：
  名称：

  Pallado 和 Platinocryptophanes 的化学和立体选择性形成

  摘要：

  环三氰基苯 (CTB) 1 在手性固定相上通过 HPLC 进行拆分，并确定其对映异构体的绝对构型。与 (+)-1 和 11 (–)-1 分开组装的光学活性钯和铂隐指，以及 [M3(dppp)3((+)-1)2](OTf )6 和 [M3(dppp) 的光学性质)3((–)-1)2](OTf )6（M = Pd 和 Pt；dppp = 1,3-双（二苯基磷酰基）丙烷）通过偏振法和电子圆二色性 (ECD) 进行了研究。金属隐象的对映体化势垒仅微弱地依赖于 16

  DOI：

  10.1002/ejic.201900230
• 作为产物：
  描述：

  copper(l) cyanide 、 (+/-)-2,7,12-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以85%的产率得到10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-tricarbonitrile
  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

• The Stereoselective Self‐Assembly of Chiral Metallo‐Organic Cryptophanes
  作者：Astrid Schaly、Yoann Rousselin、Jean‐Claude Chambron、Emmanuel Aubert、Enrique Espinosa

  DOI：10.1002/ejic.201501446

  日期：2016.2

  AbstractCryptophanes are macropolycyclic cyclophanes constructed from two triply bridged concave cyclotriveratrylene analogues that encapsulate a large range of molecular and monoatomic substrates. Self‐assembled metallo‐organic cryptophanes based on M2+–carbonitrile (M = Pd or Pt) interactions have been obtained through the reactions of chiral nitrile‐substituted cyclotribenzylenes (CTBs) 1 and 2 with [M(dppp)][OTf]2 (dppp = 1,3‐bisdiphenylphosphinopropane, OTf = triflate) in 2:3 ratios in chlorinated solvents. The cryptophanes [Pd3(dppp)3(1)2]6+ and [Pd3(dppp)3(2)2]6+ were obtained exclusively in the chiral anti form in solution at room temperature whatever solvent was used; however the meso,syn form was identified as the major isomer of [Pd3(dppp)3(1)2]6+ at low temperature in CD2Cl2, and – in the case of [Pt3(dppp)3(1)2]6+ – it formed in a minor amount at room temperature. [Pd3(dppp)3(1)2][OTf]6 and [Pt3(dppp)3(1)2][OTf]6 crystallized in the anti forms with an encapsulated chloroform molecule, and gas‐phase DFT calculations with the dispersion‐corrected B97‐D3 functional show that it is stabilized by 34.6 kJ mol–1. Interestingly, the heteroleptic cryptophane [Pd3(dppp)3(1)(2)]6+ was not detected in mixtures of [Pd(dppp)]2+ and CTBs 1 and 2 in a 3:1:1 ratio or through the equilibration of a 1:1 mixture of the preformed homoleptic cryptophanes; this points to favored self‐sorting processes.