9,9'-(biphenyl-2,2'-diyl)diacridine | 1010458-37-3

• 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'-(biphenyl-2,2'-diyl)diacridine
• 英文别名: biphenyl-2,2'-diylbis(9-acridine)；9-[2-(2-Acridin-9-ylphenyl)phenyl]acridine
• CAS: 1010458-37-3
• 化学式: C₃₈H₂₄N₂
• 分子量: 508.622
• InChiKey: HKYZBFSDXGQPDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  40
• 可旋转键数：
  3
• 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'-(biphenyl-2,2'-diyl)diacridine 、 三氟甲烷磺酸甲酯 生成
  参考文献：
  名称：

  Unprecedented four-way-output molecular response system based on biphenyl-2,2′-diyldiacridiniums: induction of axial chirality through intramolecular hydrogen bonds between chiral amide groups

  摘要：

  Upon the attachment of N-(R)-2-phenylethylamide moieties to the acridinium units of the title dication, intramolecular hydrogen bonds induce a diastereomeric preference in terms of axial chirality (70% de at -40 degrees C in CH2Cl2). Thus, external stimuli induce not only UV-vis and fluorescence spectra changes but also changes in the CD and fluorescence-detected CD (FDCD) spectra, realizing unprecedented four-way-output molecular response systems. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.179
• 作为产物：
  描述：

  10-(2-甲氧基乙氧基甲基)吖啶-9-酮 、 2,2-二碘代联苯 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 27.5h， 以53%的产率得到9,9'-(biphenyl-2,2'-diyl)diacridine
  参考文献：
  名称：

  Unprecedented four-way-output molecular response system based on biphenyl-2,2′-diyldiacridiniums: induction of axial chirality through intramolecular hydrogen bonds between chiral amide groups

  摘要：

  Upon the attachment of N-(R)-2-phenylethylamide moieties to the acridinium units of the title dication, intramolecular hydrogen bonds induce a diastereomeric preference in terms of axial chirality (70% de at -40 degrees C in CH2Cl2). Thus, external stimuli induce not only UV-vis and fluorescence spectra changes but also changes in the CD and fluorescence-detected CD (FDCD) spectra, realizing unprecedented four-way-output molecular response systems. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.179

文献信息

• Intramolecular Methylacridan-Methylacridinium Complexes with a Phenanthrene-4,5-diyl or Related Skeleton: Geometry-Property Relationships in Isolable CH Bridged Carbocations
  作者：Takanori Suzuki、Yasuyo Yoshimoto、Takashi Takeda、Hidetoshi Kawai、Kenshu Fujiwara

  DOI：10.1002/chem.200801769

  日期：2009.2.16

  Bridging the gap: Snapshots of 1,6‐H‐shift precursors indicate that a narrower CH⋅⋅⋅C+ separation (D in the ORTEP diagram) in the title complexes induces faster degenerate rearrangement of 1+. A contact distance of less than 2.7 Å is necessary to realize the organic three‐center two‐electron bond of [CHC]+, as indicated by extrapolation of the X‐ray data.

  桥接间隙：1,6-H-移的快照前体表明较窄Ç  H⋅⋅⋅C +分离（d在ORTEP图）中的标题配合物诱导的更快的退化重排1 +。小于2.7埃的接触距离是必须实现的有机三中心两电子键[C  ħ  C] +，由X射线数据的外推法所指示的。
• Unprecedented four-way-output molecular response system based on biphenyl-2,2′-diyldiacridiniums: induction of axial chirality through intramolecular hydrogen bonds between chiral amide groups
  作者：Takanori Suzuki、Kenji Ohta、Tatsuo Nehira、Hiroki Higuchi、Eisuke Ohta、Hidetoshi Kawai、Kenshu Fujiwara

  DOI：10.1016/j.tetlet.2007.11.179

  日期：2008.1

  Upon the attachment of N-(R)-2-phenylethylamide moieties to the acridinium units of the title dication, intramolecular hydrogen bonds induce a diastereomeric preference in terms of axial chirality (70% de at -40 degrees C in CH2Cl2). Thus, external stimuli induce not only UV-vis and fluorescence spectra changes but also changes in the CD and fluorescence-detected CD (FDCD) spectra, realizing unprecedented four-way-output molecular response systems. (C) 2007 Elsevier Ltd. All rights reserved.