7,8-diaza-3,3a-dihydro-3a-hydroxy-1,3-dimethylcyclopentaphenanthrene-2-one | 176373-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,8-diaza-3,3a-dihydro-3a-hydroxy-1,3-dimethylcyclopentaphenanthrene-2-one
• 英文别名: 1,11b-dihydro-11b-hydroxy-1,3-dimethyl-7,8-diazacyclopenta<1>phenanthren-2-one；3a-hydroxy-1,3-dimethyl-3H-cyclopenta[f][1,10]phenanthrolin-2-one
• CAS: 176373-93-6
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: HQMGGMAKKKQODB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.08
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7,8-diaza-3,3a-dihydro-3a-hydroxy-1,3-dimethylcyclopentaphenanthrene-2-one 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Preparation of 7,8-diazaphencyclone and its use in the construction of rigid, space-separated 1,10-phenanthroline donor–acceptor systems: new ligands for metal complexation

  摘要：

  7,8-Diazaphencyclone 7 is used as a delivery reagent to fuse 1,10-phenanthroline groups onto alkenic centres of rigid spacer molecular racks (molracs); molrac alkenes containing redox-active donor-acceptor chromophores yield molrac diads whose metal complexes, e.g. 26, are suitable for mechanistic studies involving intramolecular electron transfer.

  DOI：

  10.1039/cc9960001151
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 3-戊酮 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以73%的产率得到7,8-diaza-3,3a-dihydro-3a-hydroxy-1,3-dimethylcyclopentaphenanthrene-2-one
  参考文献：
  名称：

  Synthesis of New Rigid, Bridging Ligands for the Study of Energy and Electron-Transfer Reactions

  摘要：

  文中描述了合成和表征具有金刚烷间隔基以及两个分别连结4,5-二氮杂芴或1,10-菲咯啉鳌合单元的刚性、杆状桥联配体的过程。

  DOI：

  10.1055/s-1996-4183

文献信息

• Rigid molecular racks featuring the 1,10-phenanthroline ligand especially those co-functionalised with redox-active groups or other bidentate ligands
  作者：Ronald N. Warrener、Austin C. Schultz、Mark A. Houghton、Douglas N. Butler

  DOI：10.1016/s0040-4020(97)00014-8

  日期：1997.3

  stereospecificity. Bridged 1,10-phenanthrolines with different separation distances and ligand, ligand orientations have been prepared and mixed ligand systems are described with diazafluorene and 3,6-di(2-pyridyl)pyridazine ligand components. New diad and triad systems are reported which contain redox-active components linked to ligand centres. The rigid nature of the polyalicyclic molrac framework and the fusion

  首次制备的6,7-二氮杂苯环酮（DAPC）以二聚体形式存在，但与单体11处于热平衡状态在解决方案中。DAPC是一种反应性二烯，可与具有高立体特异性的环应变和缺电子的二烯亲核体发生反应。制备了具有不同分离距离和配体的桥连的1,10-菲咯啉，配体的取向和混合的配体体系与二氮杂芴和3,6-二（2-吡啶基）哒嗪配体组成一起描述。据报道，新的二元组和三元组系统包含与配体中心相连的氧化还原活性成分。聚脂环莫拉克骨架的刚性性质和用于连接官能团的融合方法为分子提供了精确的生色团几何定位和取向。这使得这些系统成为研究电子转移和能量转移过程的关键分子。
• The CH−π Interactions of Methyl Ethers as a Model for Carbohydrate–<i>N</i>-Heteroarene Interactions
  作者：Ping Li、Trent M. Parker、Jungwun Hwang、Fengyuan Deng、Mark D. Smith、Perry J. Pellechia、C. David Sherrill、Ken D. Shimizu

  DOI：10.1021/ol502418k

  日期：2014.10.3

  CH-pi interactions have been cited as an important contributor to carbohydrate recognition. To determine whether N-heterocycles form stronger CH-pi interactions, the interactions of methyl ether groups with heterocyclic and nonheterocyclic aromatic surfaces were studied. Both experimental and computational experiments found that N-heterocyclic aromatic surfaces formed stronger interactions. This enhancement was attributed to attractive dipole-dipole interactions between the methyl ether C-O bond and the N-heterocyclic aromatic dipole.