2-(1'-anthracenyl)-1,10-phenanthroline | 176853-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(1'-anthracenyl)-1,10-phenanthroline
• 英文别名: 2-(1-anthracenyl)-1,10-phananthroline；2-Anthracen-1-yl-1,10-phenanthroline
• CAS: 176853-45-5
• 化学式: C₂₆H₁₆N₂
• 分子量: 356.426
• InChiKey: RTYRERNTJLPMCS-UHFFFAOYSA-N

物化性质

• 沸点：
  603.7±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• 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：

  ammonium hexafluorophosphate 、 Ru(tpy)(Cl)₃ 、 2-(1'-anthracenyl)-1,10-phenanthroline 在 Et₃N 作用下， 以 乙醇 、 水 为溶剂， 以47%的产率得到2-anthracen-1-yl-1,10-phenanthroline;chlororuthenium(1+);2,6-dipyridin-2-ylpyridine;hexafluorophosphate
  参考文献：
  名称：

  Cyclometalated Complexes of Ru(II) with 2-Aryl Derivatives of Quinoline and 1,10-Phenanthroline

  摘要：

  Difficulty in cyclometalating 1-(2'-quinolinyl)pyrene and 1,3-di-(2'-quinolinyl)pyrene with Ru(H) led to a more detailed study of the cyclometalation process. A series of 2-aryl-1,10-phenanthrolines, where aryl = phenyl, 2-naphthyl, 1-anthracenyl, and 1-pyrenyl, were treated with [Ru(tPY)Cl-3] to provide either the N5Cl complex [Ru(tpy)(L)Cl](+) or this same material as a mixture with the N5C cyclometalated species [Ru(tpy)L](+). Steric effects appear to govern the ability of the ligand to attain the near planar conformation required for cyclometalation. The bridged ligand 3,1'-dimethylene-2-(2'-pyrenyl)-1,10-phenanthroline was prepared along with a quinoline analogue. The former species was found to cyclometalate at the Cl of pyrene and afford the N5Cl complex. Both the N5C (P2(1)/n (monoclinic), a = 28.1102(11), b = 8.4638(3),- c = 31.2908(12) Angstrom, Z = 8) and N5Cl (P-1 (triclinic), a = 11.7235 (10), b = 14.5306(12), c = 14.5725(12) Angstrom, Z = 2) complexes were analyzed by X-ray crystallography, and the N5Cl species evidenced a congested environment for pyrene, which is apparently stabilized by pi stacking with tpy. Similar reactions with a series of three 3,2'-bridged derivatives of 2-phenyl-1,10-phenanthroline provide both N5Cl and cyclometalated products in proportions which support the importance of,7 stacking. The electronic absorption spectra and redox potentials for these complexes evidence strong sigma donation by the cyclometalated ligand and an apparant insensitivity to the orthogonal 2-aryl group.

  DOI：

  10.1021/ic0102844
• 作为产物：
  描述：

  7-甲基-8-硝基喹啉 在 盐酸 、 氢氧化钾 、 sodium periodate 、 铁粉 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.67h， 生成 2-(1'-anthracenyl)-1,10-phenanthroline
  参考文献：
  名称：

  弗里德兰德方法学引入苯并[h]喹啉和1,10-菲咯啉亚基。

  摘要：

  已经开发了改进的8-氨基-7-喹啉甲醛的制备方法。通过先用二甲基甲酰胺二甲基乙缩醛，然后用高碘酸钠处理，可以将7-甲基-8-硝基喹啉的甲基氧化为醛。用铁还原得到氨基醛。类似的序列得到1-氨基-2-萘甲醛。喹啉衍生物与一系列乙酰基芳烃的弗里德兰德缩合反应提供了相应的2-芳基-1,10-菲咯啉。氨基醛与1,3-二乙酰基苯或2,6-二乙酰基吡啶的缩合可提供预期的Friedländer产品。对于氨基醛与1,4-二乙酰基苯，4,4'-二乙酰基联苯，1,5-二乙酰基蒽，1,2,3,4,5,6,7,8-八氢ac啶-1的反应描述了相似的化学方法8-dione和四环[6.3.0.0。（4,11）0（5，

  DOI：

  10.1021/jo952164h

文献信息

• Introduction of Benzo[<i>h</i>]quinoline and 1,10-Phenanthroline Subunits by Friedländer Methodology
  作者：Elvira C. Riesgo、Xiaoqing Jin、Randolph P. Thummel

  DOI：10.1021/jo952164h

  日期：1996.1.1

  8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedländer condensation of the quinoline derivative with a series of acetylaromatics

  已经开发了改进的8-氨基-7-喹啉甲醛的制备方法。通过先用二甲基甲酰胺二甲基乙缩醛，然后用高碘酸钠处理，可以将7-甲基-8-硝基喹啉的甲基氧化为醛。用铁还原得到氨基醛。类似的序列得到1-氨基-2-萘甲醛。喹啉衍生物与一系列乙酰基芳烃的弗里德兰德缩合反应提供了相应的2-芳基-1,10-菲咯啉。氨基醛与1,3-二乙酰基苯或2,6-二乙酰基吡啶的缩合可提供预期的Friedländer产品。对于氨基醛与1,4-二乙酰基苯，4,4'-二乙酰基联苯，1,5-二乙酰基蒽，1,2,3,4,5,6,7,8-八氢ac啶-1的反应描述了相似的化学方法8-dione和四环[6.3.0.0。（4,11）0（5，
• Cyclometalated Complexes of Ru(II) with 2-Aryl Derivatives of Quinoline and 1,10-Phenanthroline
  作者：Céline Bonnefous、Abdellatif Chouai、Randolph P. Thummel

  DOI：10.1021/ic0102844

  日期：2001.11.1

  Difficulty in cyclometalating 1-(2'-quinolinyl)pyrene and 1,3-di-(2'-quinolinyl)pyrene with Ru(H) led to a more detailed study of the cyclometalation process. A series of 2-aryl-1,10-phenanthrolines, where aryl = phenyl, 2-naphthyl, 1-anthracenyl, and 1-pyrenyl, were treated with [Ru(tPY)Cl-3] to provide either the N5Cl complex [Ru(tpy)(L)Cl](+) or this same material as a mixture with the N5C cyclometalated species [Ru(tpy)L](+). Steric effects appear to govern the ability of the ligand to attain the near planar conformation required for cyclometalation. The bridged ligand 3,1'-dimethylene-2-(2'-pyrenyl)-1,10-phenanthroline was prepared along with a quinoline analogue. The former species was found to cyclometalate at the Cl of pyrene and afford the N5Cl complex. Both the N5C (P2(1)/n (monoclinic), a = 28.1102(11), b = 8.4638(3),- c = 31.2908(12) Angstrom, Z = 8) and N5Cl (P-1 (triclinic), a = 11.7235 (10), b = 14.5306(12), c = 14.5725(12) Angstrom, Z = 2) complexes were analyzed by X-ray crystallography, and the N5Cl species evidenced a congested environment for pyrene, which is apparently stabilized by pi stacking with tpy. Similar reactions with a series of three 3,2'-bridged derivatives of 2-phenyl-1,10-phenanthroline provide both N5Cl and cyclometalated products in proportions which support the importance of,7 stacking. The electronic absorption spectra and redox potentials for these complexes evidence strong sigma donation by the cyclometalated ligand and an apparant insensitivity to the orthogonal 2-aryl group.