9-[8-(10-methylacridan-9-yl-9-d)naphthalen-1-yl]acridine | 862856-30-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 9-[8-(10-methylacridan-9-yl-9-d)naphthalen-1-yl]acridine
• CAS: 862856-30-2
• 化学式: C₃₇H₂₆N₂
• 分子量: 499.619
• InChiKey: JPOPVUXVOCOUAX-QUBACOGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.47
• 重原子数：
  39.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-[8-(10-methylacridan-9-yl-9-d)naphthalen-1-yl]acridine 、 三氟甲烷磺酸甲酯 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 苯 为溶剂， 反应 1.33h， 以68%的产率得到10-methyl-9-[8-(10-methylacridan-9-yl-9-d)naphthalen-1-yl]acridinium triflate
  参考文献：
  名称：

  Isolation and Low-Temperature X-ray Analysis of Intramolecular Triarylmethane−Triarylmethylium Complex:  Preference for a C−H-Bridged Unsymmetric Structure Exhibiting a Facile 1,5-Hydride Shift and Charge-Transfer Interaction

  摘要：

  The intramolecular triarylmethane-methylium complex with an averaged C2v-symmetry was successfully generated by N-methylation of the acridine-acridan hybrid. Theoretical calculation and VT-NMR analyses in solution indicate the unsymmetric geometry for the three-center bond, which was finally confirmed crystallographically. Significant degree of CT interaction is induced through the very short C-H...C+ contact.

  DOI：

  10.1021/ja053161h
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 正丁基锂 、 三溴氧磷 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 88.25h， 生成 9-[8-(10-methylacridan-9-yl-9-d)naphthalen-1-yl]acridine
  参考文献：
  名称：

  Isolation and Low-Temperature X-ray Analysis of Intramolecular Triarylmethane−Triarylmethylium Complex:  Preference for a C−H-Bridged Unsymmetric Structure Exhibiting a Facile 1,5-Hydride Shift and Charge-Transfer Interaction

  摘要：

  The intramolecular triarylmethane-methylium complex with an averaged C2v-symmetry was successfully generated by N-methylation of the acridine-acridan hybrid. Theoretical calculation and VT-NMR analyses in solution indicate the unsymmetric geometry for the three-center bond, which was finally confirmed crystallographically. Significant degree of CT interaction is induced through the very short C-H...C+ contact.

  DOI：

  10.1021/ja053161h

文献信息

• Intramolecular Triarylmethane–Triarylmethylium Complexes with a Naphthalene-1,8-diyl Skeleton: Isolation, Structure, and Reactivities of the CH-Bridged Carbocations
  作者：Takashi Takeda、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1002/chem.200700803

  日期：2007.9.28

  um complexes with a naphthalene-1,8-diyl-type skeleton have been achieved. These bridged cations prefer a C--H localized structure both in solution and in the solid state. The bridging hydrogen undergoes a facile intramolecular 1,5-hydride shift from one carbon to another in solution. The C--H delocalized geometry is suggested to be the transition-state structure of the degenerate rearrangement. Charge-transfer

  具有萘-1,8-二基型骨架的分子内三芳基甲烷-三芳基甲基鎓配合物的分离和低温X射线分析已实现。这些桥连的阳离子在溶液和固态中均更倾向于CH局部结构。桥接的氢在溶液中经历从一个碳到另一个碳的容易的分子内1，5-氢化物转变。建议将CH杂化的几何结构是简并重排的过渡态结构。从三芳基甲烷到三芳基甲基鎓单元的电荷转移相互作用在电子光谱中是明显的。这种相互作用稳定了目前的阳离子。对布朗斯台德酸的低反应性表明，这些物质不是1,1,2,2-四芳基萘衍生物在酸辅助的长键裂解中的反应中间体。