N-(2'-methylphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide | 137093-53-9

• 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: N-(2'-methylphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide
• 英文别名: 17-(2-Methylphenyl)-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-(2-methylphenyl)-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 137093-53-9；59252-50-5
• 化学式: C₂₅H₁₉NO₂
• 分子量: 365.431
• InChiKey: MLJBOPMJMWOBPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  N-(2'-methylphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide 在 吡啶 、 sodium tetrahydroborate 、 硫酸 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 rac-(9R,10S,11S,12R,15R)-14-oxo-13-(o-tolyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracen-12-yl benzoate
  参考文献：
  名称：

  Singh, Narain; Verma, Shiva Mohan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 10, p. 873 - 877

  摘要：

  DOI：
• 作为产物：
  描述：

  dibenzobarallene 、 邻甲苯胺 反应 3.0h， 生成 N-(2'-methylphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide
  参考文献：
  名称：

  的结构研究ñ - （2'-取代的苯基）-9,10-二氢-9,10- ethanoanthracene -11,12-二甲酰亚胺通过X射线衍射和NMR光谱，证明在液相和固相CH /π相互作用

  摘要：

  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[

  DOI：

  10.1039/b300759f

文献信息

• Aliphatic C-H/π and Heteroatom/π Interactions in<i>N</i>-Aryl-3,4-(9′,10′-dihydroanthracene-9′,10′-diyl)succinimides
  作者：Laura Raimondi、Maurizio Benaglia、Franco Cozzi

  DOI：10.1002/ejoc.201402288

  日期：2014.8

  these systems the aliphatic C–H/π interaction is mildly stabilizing and, to a certain extent, capable of overcoming unfavorable steric effects. On the other hand, the interaction of a π system with oxygen, sulfur, or fluorine atoms was destabilizing. When methyl or ethyl groups were allowed to compete with oxygen and fluorine for interaction with the benzene ring, C–H/π interactions were consistently

  合成了一系列 N-aryl-3,4-(9',10'-dihydroanthracene-9',10'-diyl)succinimides 作为模型化合物，以研究芳香族 π 系统与脂肪族 H 原子和杂原子的相互作用如氧、硫、氟等。刚性支架的空间要求迫使二氢蒽基部分的 N-芳基残基和苯环采用边对面构象，其中 N-芳基的邻位取代基之一与 π 系统相互作用。琥珀酰亚胺通常作为异构体的混合物获得，它们的比例被认为是 N-芳基残基邻位取代模式的函数。实验观察到的比率与 BMK/cc-pVDZ 理论水平的 DFT 计算预测的比率非常一致。从这项研究得出的结论是，在这些系统中，脂肪族 C-H/π 相互作用具有温和的稳定性，并且在一定程度上能够克服不利的空间效应。另一方面，π 系统与氧、硫或氟原子的相互作用是不稳定的。当允许甲基或乙基与氧和氟竞争与苯环的相互作用时，尽管存在不利的空间效应，但一致观察到 C-H/π
• 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.
• Srivastav, Kamal K.; Verma, Ashok K.; Verma, Shiva M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 11, p. 1143 - 1148
  作者：Srivastav, Kamal K.、Verma, Ashok K.、Verma, Shiva M.

  DOI：——

  日期：——
• SINGH, N.;VERMA, S. M., INDIAN J. CHEM., 1981, 20, N 10, 873-877
  作者：SINGH, N.、VERMA, S. M.

  DOI：——

  日期：——
• Singh, Narain; Verma, Shiva Mohan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 10, p. 873 - 877
  作者：Singh, Narain、Verma, Shiva Mohan

  DOI：——

  日期：——