9,9'-(Naphthalene-1,8-diyl)bis(acridine) | 797056-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9,9'-(Naphthalene-1,8-diyl)bis(acridine)
• 英文别名: 9,9'-(naphthalene-1,8-diyl)bisacridine；9,9'-(naphthalene-1,8-diyl)diacridine；9-(8-Acridin-9-ylnaphthalen-1-yl)acridine；9-(8-acridin-9-ylnaphthalen-1-yl)acridine
• CAS: 797056-31-6
• 化学式: C₃₆H₂₂N₂
• 分子量: 482.584
• InChiKey: PZXQDEPAJYDMBN-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C (decomp)(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  654.9±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9'-(Naphthalene-1,8-diyl)bis(acridine) 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 47.33h， 生成 10-methyl-9-[8-(10-methylacridan-9-yl)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 为溶剂， 反应 42.25h， 生成 9,9'-(Naphthalene-1,8-diyl)bis(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。
• Short nonbond and long C–C bond in naphthalene-1,8-diylbis(10-methylacridinium) and the corresponding hexaphenylethane derivative: a new electrochromic pair exhibiting dynamic redox properties
  作者：Hidetoshi Kawai、Takashi Takeda、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1016/j.tetlet.2004.09.071

  日期：2004.11

  The extremely long C–C bond [1.696(3) Å] in the colorless dispiroacenaphthene-type hexaphenylethane is cleaved readily upon electrochemical transformation into the orange colored naphthalene-1,8-diylbis(acridinium), in which the two cationic units are forced to overlap in a face-to-face manner exhibiting the shortest C+ ⋯ C+ interatomic contact of 2.927(7) Å among the values ever reported.

  无色双螺ac基六苯基乙烷中极长的C–C键[1.696（3）Å]在电化学转化为橙色萘-1,8-二基双（时很容易裂解，其中两个阳离子单元被迫以面对面的方式重叠，显示出有史以来最短的C +  ⋯C +原子间接触，为2.927（7）Å。
• Ultralong Carbon–Carbon Bonds in Dispirobis(10‐methylacridan) Derivatives with an Acenaphthene, Pyracene, or Dihydropyracylene Skeleton
  作者：Hidetoshi Kawai、Takashi Takeda、Kenshu Fujiwara、Makoto Wakeshima、Yukio Hinatsu、Takanori Suzuki

  DOI：10.1002/chem.200702028

  日期：2008.6.27

  Acenapthalene, pyracene, and dihydropyracylene attached to two units of spiroacridan are a novel class of hexaphenylethane (HPE) derivatives that have an ultralong Csp3-Csp3 bond (1.77-1.70 A). These sterically challenged molecules were cleanly prepared by C-C bond formation through two-electron reduction from the less-hindered dications. These ultralong bonds were realized based on several molecular-design

  连接到螺菌oa啶两个单元上的庚烯，并四苯和二氢次萘并茂是具有超长Csp3-Csp3键（1.77-1.70 A）的新型六苯基乙烷（HPE）衍生物。这些空间挑战的分子是通过从较不受阻碍的指示通过双电子还原形成CC键来干净地制备的。这些超长键是基于几种分子设计概念而实现的，这些概念包括通过融合或桥接HPE分子中的芳基，通过“多重钳制”增强“前应变”。这些超长键的长度及其与构象的关系（扭转角）也通过理论计算得到了验证。
• ATROPISOMERIC 1,8-BISPHENOLNAPTHALENES AND THEIR USE IN ENANTIOSELECTIVE RECOGNITION AND ASYMMETRIC SYNTHESIS
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20140128637A1

  公开（公告）日：2014-05-08

  This invention related to atropisomeric 1,8-bisphenolnaphthalenes and derivatives thereof of the general formula (I): which are useful in resolution of enantiomers, enantioselective recognition and asymmetric synthesis.

  本发明涉及一般式(I)的异构体1,8-双酚萘及其衍生物，这些化合物在对映体分离、对映选择性识别和不对称合成中有用。
• US9085511B2
  申请人：——

  公开号：US9085511B2

  公开（公告）日：2015-07-21