9,13-diphenyl-11-(o-tolyl)-9,9a,12a,13-tetrahydro-10H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(11H)-trione | 220324-93-6

• 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: 9,13-diphenyl-11-(o-tolyl)-9,9a,12a,13-tetrahydro-10H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(11H)-trione
• 英文别名: 9,13-diphenyl-11-(o-tolyl)-9,9a,12a,13-tetrahydro-10H-9,13-epoxyphenanthro[9,10-f]isoindole-10,12(11H)-dione；(1S,16R,17R,21S)-19-(2-methylphenyl)-1,16-diphenyl-19-azahexacyclo[14.5.1.02,15.03,8.09,14.017,21]docosa-2(15),3,5,7,9,11,13-heptaene-18,20,22-trione
• CAS: 220324-93-6
• 化学式: C₄₀H₂₇NO₃
• 分子量: 569.659
• InChiKey: VIHSWTCGONXTPE-DFEXOLERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对二甲苯 、 9,13-diphenyl-11-(o-tolyl)-9,9a,12a,13-tetrahydro-10H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(11H)-trione 生成
  参考文献：
  名称：

  Phencyclone Diels-Alder adducts as a new crystalline host. Role of CH···π and CH···O interactions

  摘要：

  A series of crystalline host compounds, which have a bicyclo[2.2.1]heptene-7-one system, has been synthesized and their inclusion behavior has been investigated. The cycloadduct of phencyclone and N-naphthylmaleimide forms a 1:1 crystalline inclusion complex with 2-butanone. The crystal structure indicates the presence of weak lattice forces supported by C-H ...pi and C-H ... O interactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02283-7
• 作为产物：
  描述：

  9,10-菲并1,12-二苯基环戊二烯酮 以 溶剂黄146 、 甲苯 为溶剂， 生成 9,13-diphenyl-11-(o-tolyl)-9,9a,12a,13-tetrahydro-10H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(11H)-trione
  参考文献：
  名称：

  Do Deuteriums Form Stronger CH−π Interactions?

  摘要：

  The D/H isotope effect for the CH-pi interaction was studied experimentally and computationally. First, a series of molecular balances that are very sensitive to changes in the strength of the CH-pi interactions in solution were designed. Balances with deuterated and non-deuterated alkyl groups were synthesized, and their intramolecular CH-pi interactions were compared. The geometries of their intramolecular CH-pi and CD-pi interactions were characterized in the solid state by X-ray analysis, and the strength of each interaction was characterized in solution by the folded/unfolded ratio as measured by H-1 NMR spectra. Second, the relative strengths of the CH-pi and CD-pi interactions were also assessed computationally using dispersion-corrected DFT (PDE-D2/6-31+G*). No significant differencee was observed in either the experimental or theoretical studies, indicating that the D/H isotope effect for the CH-pi interaction is either very small or nonexistent.

  DOI：

  10.1021/ja305788p

文献信息

• Non-hydroxylic clathrate hosts of [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides: recognition of aromatic guests
  作者：Yasuyuki Yoshitake、Junichi Misaka、Koji Setoguchi、Masaki Abe、Tomohiro Kawaji、Masashi Eto、Kazunobu Harano

  DOI：10.1039/b201915a

  日期：——

  A series of non-hydroxylic crystalline host compounds, [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides having a bicyclo[2.2.1]heptene-7-one system, was synthesized and their inclusion behavior investigated. X-Ray crystal analyses of the inclusion compounds of the N-(1-naphthyl) derivative with butan-2-one, the N-(m-tolyl) derivative with p-xylene, together with the guest-free host and the N-(p-tolyl) derivative with m-xylene indicate that the “space” surrounded by the phenanthrene ring, two phenyl rings and bridge carbonyl of the 1,3-diphenyl-1,3-dihydrocyclopenta[l]phenanthren-2-one moiety plays an important role, not only in the formation of inclusion complexes with the aromatic guests but also in host–host interactions. In every case, the N-aryl succinimide assists complex formation with the guests, in which the weak lattice forces due to C–H⋯π and C–H⋯O interactions are operative. Methyl-substituted benzenes are effectively recognized by the C–H⋯π interactions between the guest molecules and the phenanthrene ring of the hosts.

  合成了一系列非羟基结晶主客体化合物，即含有二环[2.2.1]庚烯-7-酮体系的苯并环戊烯和N-芳基马来酰亚胺的[4 + 2]π环加成产物，并研究了它们的包埋行为。对N-(1-萘基)衍生物与丁酮、N-(m-甲苯基)衍生物与对二甲苯的包埋化合物，以及无客体的主客体和N-(p-甲苯基)衍生物与米二甲苯的X射线晶体分析表明，1,3-二苯基-1,3-氢环戊烯-2-酮部分中由菲环、两个苯环和桥碳酰基所包围的“空间”在与芳香族客体形成包埋复合物以及主客体之间的相互作用中发挥了重要作用。在每种情况下，N-芳基琥珀酰亚胺都有助于与客体的复合物形成，其中由于C–H⋯π和C–H⋯O相互作用而产生的微弱晶格力起作用。甲基取代的苯类化合物通过客体分子与主客体的菲环之间的C–H⋯π相互作用得到了有效识别。
• Direct Experimental Evidence for Halogen-Aryl π Interactions in Solution from Molecular Torsion Balances
  作者：Han Sun、André Horatscheck、Vera Martos、Max Bartetzko、Ulrike Uhrig、Dieter Lentz、Peter Schmieder、Marc Nazaré

  DOI：10.1002/anie.201700520

  日期：2017.6.1

  dissected halogen–aryl π interactions experimentally using a bicyclic N-arylimide based molecular torsion balances system, which is based on the influence of the non-bonded interaction on the equilibria between folded and unfolded states. Through comparison of balances modulated by higher halogens with fluorine balances, we determined the magnitude of the halogen–aryl π interactions in our unimolecular

  我们使用基于双环N-芳基酰亚胺的分子扭转平衡系统实验性地分析了卤素-芳基π相互作用，该系统基于非键相互作用对折叠状态和未折叠状态之间的平衡的影响。通过比较高级卤素调节的平衡与氟平衡，我们确定了我们单分子体系中卤素-芳基π相互作用的幅度大于-5.0 kJ mol -1，这与生物分子体系中估计的幅度相当。我们的研究提供了溶液中卤素-芳基π相互作用的直接实验证据，到目前为止，该相互作用仅在固态下才得以揭示，并通过量子力学计算从理论上进行了评估。
• Experimental Study of the Cooperativity of CH−π Interactions
  作者：Chen Zhao、Ping Li、Mark D. Smith、Perry J. Pellechia、Ken D. Shimizu

  DOI：10.1021/ol5014729

  日期：2014.7.3

  A series of new torsional molecular balances was designed to study the cooperativity of CH-pi interaction in the solid state and in solution. The measured interaction energies correlated better to the number of participating alkyl carbons than to the number of CH-pi contacts. The methyl and ethyl groups displayed additive interaction energies. However, the branched isopropyl group displayed strong positive cooperativity with higher than predicted interaction energies.