2,3:5,6-dibenzobicyclo[2.2.2]octane-7,8-(N-phenyl)dicarboxylic imide | 137092-85-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 2,3:5,6-dibenzobicyclo[2.2.2]octane-7,8-(N-phenyl)dicarboxylic imide
• 英文别名: N-phenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide；N-Phenyl-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid；17-Phenyl-17-azapentacyclo[6.6.5.0~2,7~.0~9,14~.0~15,19~]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione (non-preferred name)；17-phenyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 137092-85-4；4697-05-6
• 化学式: C₂₄H₁₇NO₂
• mdl: MFCD00367610
• 分子量: 351.404
• InChiKey: IBFKTUXGPUONQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3:5,6-dibenzobicyclo[2.2.2]octane-7,8-(N-phenyl)dicarboxylic imide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 以75%的产率得到17-Phenyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene
  参考文献：
  名称：

  含有三蝶烯刚性立体结构的发色团分子及其合 成方法和应用

  摘要：

  本发明涉及含有三蝶烯刚性立体结构的发色团分子及其合成方法，以及该含有三蝶烯刚性立体结构的发色团分子在聚合物电光材料中的应用。本发明是利用N-苯基马来酰亚胺与蒽的环加成反应，再通过反应连接上如“碳碳双键”或“噻吩类”结构的电子桥部分和如“三氰基呋喃”或“三氰基吡咯啉”结构的电子受体部分，得到结构如下所示的含有三蝶烯三维刚性立体结构的发色团分子。将本发明的含有三蝶烯刚性立体结构的发色团分子掺杂至聚合物(如无定型聚碳酸酯APC)中，经极化处理，可得到高性能的聚合物电光材料。本发明的含有三蝶烯刚性立体结构的发色团分子易于合成和分离。

  公开号：

  CN103373990B
• 作为产物：
  描述：

  蒽 在 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 3.0h， 生成 2,3:5,6-dibenzobicyclo[2.2.2]octane-7,8-(N-phenyl)dicarboxylic imide
  参考文献：
  名称：

  Synthesis, characterization, and antibacterial activity of a new poly azo compound containing N-arylsuccinimid and dibenzobarrelene moieties

  摘要：

  摘要 本研究介绍了一种新的多偶氮化合物的合成、表征和抗菌活性评估，该化合物是由先前报道的 N-芳基琥珀酰亚胺前体 5 与苯胺的重氮离子偶联而成。利用物理、元素、一维和二维光谱数据对这种偶氮化合物进行了表征。新型偶氮化合物 7（最低抑菌浓度 [MIC] = 16-32 μg/mL）的抗菌活性高于其前体 5（MIC = 32-64 μg/mL），但与参考药物环丙沙星（MIC = 0.5-4 μg/mL）相比则较低。

  DOI：

  10.1515/hc-2022-0157

文献信息

• Fluorous Dienophiles Are Powerful Diene Scavengers in Diels−Alder Reactions
  作者：Stefan Werner、Dennis P. Curran

  DOI：10.1021/ol035214a

  日期：2003.9.1

  [reaction: see text] Three fluorous dienophiles have been synthesized, and their value in scavenging an excess diene after Diels-Alder reactions is shown. The resulting fluorous derivatives are separated by solid-phase extraction on fluorous silica gel (FSPE). The fluorous [1,2,4]triazoline-3,5-dione 10 reacted with most dienes within seconds or minutes.

  [反应：见正文]合成了三种氟二烯亲核体，并显示了它们在Diels-Alder反应后清除过量二烯的价值。通过在氟硅胶（FSPE）上进行固相萃取来分离所得的氟衍生物。氟[1,2,4]三唑啉-3,5-二酮10在数秒或数分钟内与大多数二烯反应。
• Design, Synthesis and Biochemical Evaluation of Novel Ethanoanthracenes and Related Compounds to Target Burkitt’s Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、James P. McKeown、John E. O’Brien、Brendan Twamley、Darren Fayne、D. Clive Williams、Mary J. Meegan

  DOI：10.3390/ph13010016

  日期：——

  Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75. Structural modifications were achieved by Diels-Alder

  淋巴瘤（淋巴系统癌）占全世界恶性疾病的12％。伯基特氏淋巴瘤（BL）是非霍奇金淋巴瘤的一种罕见形式，其癌症始于免疫B细胞。我们报告了9,10-dihydro-9,10-ethanananthracene基化合物与抗抑郁药Maprotiline对BL细胞系MUTU-1和DG-75结构相关的化合物的合成和抗增殖活性的初步研究。通过使9-（2-硝基乙烯基）蒽核心与许多亲二烯体包括马来酸酐，马来酰亚胺，丙烯腈和苯炔的狄尔斯-阿尔德反应进行结构修饰。在BL细胞系EBV- MUTU-1和EBV + DG-75（耐化学性）中评估了这些化合物的抗增殖活性。最有效的化合物13j，15、16a，16b，16c，图16d和19a显示的相对于BL细胞系EBV- MUTU-1的IC50值在0.17–0.38μM范围内，相对于耐化学性BL细胞系EBV + DG-75的IC50值在0.45–0.78μM范围内。化合物1
• Structural studies of N-(2′-substituted phenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximides by X-ray diffraction and NMR spectroscopy—proofs for CH/π interactions in liquid and solid phases
  作者：Gisbert Grossmann、Marek J. Potrzebowski、Sebastian Olejniczak、Natasza E. Ziółkowska、Grzegorz D. Bujacz、Wlodzimierz Ciesielski、Wiktor Prezdo、Valerii Nazarov、Vladislav Golovko

  DOI：10.1039/b300759f

  日期：——

  weak intermolecular CH/π contacts were found in 2 and 3, while anti and syn conformations coexist in 1 with CH/π contacts being absent. Solid-state 13C CP/MAS spectra confirm the X-ray molecular structural data. Two crystallographically independent molecules in the unit cell of 2 correspond to two isotropic chemical shifts for C atoms in the CP/MAS spectrum. The different molecular dynamics of both

  N-（2'- R-苯基）-9,10-二氢-9,10-乙基蒽-11,12-二甲叉酰亚胺，R = Me（1），OMe（2），OEt（3）和H（4）被调查了。的晶体和分子结构1 - 3，通过单晶的方法测定，显示出的不同构象ñ - （2'- - [R -苯基）基团。反构象和弱的分子间CH /π触点中发现2和3，而抗和顺式构象中共存1缺少CH /π触点。固态13 C CP / MAS光谱确认X射线分子结构数据。在的单元电池的两个晶体学上独立的分子2对应于用于在CP / MAS光谱个C原子的两块各向同性化学位移。在不同的交叉极化曲线中，由热因子和分子间CH /π接触指示的两个分子在2晶格中的不同分子动力学清晰可见。这核磁共振4的数据表明苯基 环键合到 氮与乙基羧酰亚胺环几乎共面。完全分配液态1 H和13 C NMR谱的1 - 4有可能通过应用高场核磁共振 光谱学。修改了文献中13 C化学位移的一些错误分配。溶液中[
• Modular design of hosts involving a rigid succinimide framework and N-bonded lateral groups. Crystalline inclusion properties and crystal structures of inclusion compounds with dioxane, methanol, and DMF
  作者：Edwin Weber、Stephan Finge、Ingeborg Csoeregh

  DOI：10.1021/jo00026a018

  日期：1991.12

  A series of crystalline host molecules comprising a characteristic 9,10-ethanoanthracene-11,12-dicarboxamide framework have been synthesized and studied with regard to their inclusion behavior. They follow a new design concept which is to convert a given molecule, presently of amine, aminophenol, amino alcohol, or amino acid type, by addition of a so-called "clathratogenic group" (inclusion promoting group) into a crystalline host. These hosts form crystalline inclusion compounds with a variety of uncharged organic molecules ranging from protic dipolar to rather apolar compounds (103 different inclusion species). Inclusion formation and binding modes depend on the structural features of the hosts, i.e., the type of functional groups, their number, and geometric factors. X-ray crystal structures of three inclusion species are reported: 1.dioxane (1:1) [P2(1)/n, a = 11.9757 (4) angstrom, b = 9.8442 (3) angstrom, c = 16.2371 (5) angstrom, beta = 109.196 (4)-degrees, Z = 4], 23.MeOH (1:1) [Pbca, a = 8.532 (1) angstrom, b = 18.865 (1) angstrom, c = 24.074 (2) angstrom, Z = 8], 24.DMF (1:1) [P2(1)/a, a = 15.217 (1) angstrom, b = 11.445 (1) angstrom, c = 26.685 (2) angstrom, beta = 106.15 (1)-degrees, Z = 8]. They show the compounds to be typical coordinatoclathrates with hydrogen bond interactions between host and guest. In the crystals of 1.dioxane (1:1), hydrophobically aggregated host molecules form rectangular cages, each with space enough for two H bonded guests. In 23.MeOH (1:1), the guest acts both as donor and acceptor in H bonds, resulting in endless H bonded chains of alternating host and guest molecules. The finite 1:1 host-guest associates in 24.DMF (1:1) are held together by characteristic O-H...O(C) and possibly als by (C)H...O-type interactions.
• Photoactivatable Anthracenes
  作者：Ek Raj Thapaliya、Burjor Captain、Françisco M. Raymo

  DOI：10.1021/jo5004482

  日期：2014.5.2

  Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.