9-N-benzyl-1-oxophenalene | 670223-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 9-N-benzyl-1-oxophenalene
• 英文别名: 9-(benzylamino)-1H-phenalen-1-one；9-(Benzylamino)-1H-phenalen-1-one；9-(benzylamino)phenalen-1-one
• CAS: 670223-98-0
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: IYOABNFVEYPDRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-N-benzyl-1-oxophenalene 在 三氯化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以96%的产率得到
  参考文献：
  名称：

  第一种一维苯基基中性自由基分子导体的合成、结构和物理性质

  摘要：

  我们报告了苄基取代的螺二苯萘基自由基的制备、结晶和固态表征。晶体结构显示自由基在固态下是单体，分子以不寻常的一维 (1-D) 方式堆积，我们将其称为 pi 阶跃堆叠。这种特殊的一维堆叠模式通过正交苯基单元的存在而强制在晶格排列上，这些单元专门用于防止低维结构的结晶。结构表明这种策略是有效的，堆栈中的相邻分子只能通过每个苯二烯基单元一对活性（自旋）碳原子的重叠进行相互作用，导致 pi-step 结构，其中每个苯二烯基单元的剩余四个活性碳原子不与最近的相邻分子相互作用。4-360 K 温度范围内的磁化率数据可能适合具有链内自旋耦合 J = -52.3 cm(-1) 的反铁磁海森堡 S = 1/2 线性链模型。尽管堆叠均匀，但该材料的室温电导率为 1.4 x 10(-3) S/cm，最好将其描述为莫特绝缘体。

  DOI：

  10.1021/ja037864f
• 作为产物：
  描述：

  9-羟基-萘嵌苯-1-酮 在 potassium phosphate 作用下， 以 水 、 甲苯 为溶剂， 反应 7.0h， 生成 9-N-benzyl-1-oxophenalene
  参考文献：
  名称：

  Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents

  摘要：

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.032

文献信息

• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis, Structure and Physical Properties of the First One-Dimensional Phenalenyl-Based Neutral Radical Molecular Conductor
  作者：S. K. Pal、M. E. Itkis、R. W. Reed、R. T. Oakley、A. W. Cordes、F. S. Tham、T. Siegrist、R. C. Haddon

  DOI：10.1021/ja037864f

  日期：2004.2.1

  We report the preparation, crystallization, and solid-state characterization of a benzyl-substituted spirobiphenalenyl radical. The crystal structure shows that the radical is monomeric in the solid state, with the molecules packed in an unusual one-dimensional (1-D) fashion that we refer to as a pi-step stack. This particular mode of 1-D stacking is forced on the lattice arrangement by the presence

  我们报告了苄基取代的螺二苯萘基自由基的制备、结晶和固态表征。晶体结构显示自由基在固态下是单体，分子以不寻常的一维 (1-D) 方式堆积，我们将其称为 pi 阶跃堆叠。这种特殊的一维堆叠模式通过正交苯基单元的存在而强制在晶格排列上，这些单元专门用于防止低维结构的结晶。结构表明这种策略是有效的，堆栈中的相邻分子只能通过每个苯二烯基单元一对活性（自旋）碳原子的重叠进行相互作用，导致 pi-step 结构，其中每个苯二烯基单元的剩余四个活性碳原子不与最近的相邻分子相互作用。4-360 K 温度范围内的磁化率数据可能适合具有链内自旋耦合 J = -52.3 cm(-1) 的反铁磁海森堡 S = 1/2 线性链模型。尽管堆叠均匀，但该材料的室温电导率为 1.4 x 10(-3) S/cm，最好将其描述为莫特绝缘体。