acridine orange | 32360-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: acridine orange
• 英文别名: 2-N,2-N,7-N,7-N-tetramethylanthracene-2,7-diamine
• CAS: 32360-71-7
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: ATMYOMIARHLPCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2.7-Bis-dimethylamino-9.10-dihydro-anthracen 在 四氯苯醌 作用下， 以 甲醇 为溶剂， 生成 acridine orange
  参考文献：
  名称：

  二芳基和三芳基甲烷染料的立体效应。第十部分。孔雀石绿和结晶紫的桥接衍生物的电子吸收光谱

  摘要：

  为了确定分子构象，已将异亚丙基单独和双重引入孔雀绿和结晶紫的邻位。讨论这些染料的电子吸收光谱时，特别要参考它们对孔雀石绿邻位衍生物第一带的强度变化的影响。在孔雀石绿和结晶紫中引入两个异亚丙基桥会产生相当大的红移，这只能归因于芳基核的扭曲。

  DOI：

  10.1039/j29710000319

文献信息

• Steric effects in di- and tri-arylmethane dyes. Part X. Electronic absorption spectra of bridged derivatives of malachite green and crystal violet
  作者：C. Aaron、C. C. Barker

  DOI：10.1039/j29710000319

  日期：——

  The isopropylidene group has been introduced singly and doubly into ortho-positions of Malachite Green and Crystal Violet in order to determine molecular conformation. The electronic absorption spectra of these dyes are discussed with particular reference to their bearing on intensity variations of the first band of ortho-derivatives of Malachite Green. The introduction of two isopropylidene bridges

  为了确定分子构象，已将异亚丙基单独和双重引入孔雀绿和结晶紫的邻位。讨论这些染料的电子吸收光谱时，特别要参考它们对孔雀石绿邻位衍生物第一带的强度变化的影响。在孔雀石绿和结晶紫中引入两个异亚丙基桥会产生相当大的红移，这只能归因于芳基核的扭曲。
• Facile Syntheses of 1,8-Bis(diphenylphosphino)anthracene and 1,8-Bis(dimethylamino)anthracene by Nucleophilic Substitution of 1,8-Difluoroanthracene
  作者：Matthias W. Haenel、Stephan Oevers、Joachim Bruckmann、Jörg Kuhnigk、Carl Krüger

  DOI：10.1055/s-1998-1627

  日期：1998.3

  1,8-Bis(diphenylphosphino)anthracene (1) was prepared in a three-step synthesis in 51% overall yield starting from 1,8-dichloro-9,10-anthraquinone (8). Compound 8 was converted by chlorine-fluorine exchange and reduction with zinc into 1,8-difluoroanthracene (7) from which 1 was obtained by reaction with potassium 1,8-bis(dimethylamino)anthracene (10) clearly showed that in the case of 7 direct nucleophilic displacement (addition-elimination mechanism) dominates over aryne formation (elimination-addition mechanism). Single crystal X-ray structure analyses are reported for 1 and 10.

  以 1,8-二氯-9,10-蒽醌 (8) 为原料，通过三步合成制备了 1,8-双(二苯基膦)蒽 (1)，总产率为 51%。化合物8通过氯-氟交换并用锌还原转化为1,8-二氟蒽(7)，其中1通过与1,8-双(二甲氨基)蒽钾(10)反应得到，清楚地表明在7 直接亲核置换（加成-消除机制）主导芳炔形成（消除-加成机制）。报道了 1 和 10 的单晶 X 射线结构分析。
• Nitrogen–Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole
  作者：Ming Wang、Qiaoling Fan、Xuefeng Jiang

  DOI：10.1021/acs.orglett.7b03564

  日期：2018.1.5

  A nitrogen iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a non steroidal anti-inflammatory drug) were efficiently established through this protocol.
• KISSANE P. J.; JOHNS S. R.; WILLING R. I.; SASSE W. H. F., AUSTRAL. J. CHEM. <JAJCH-AS>, 1976, 29, NO 7, 1613-1616
  作者：KISSANE P. J.、 JOHNS S. R.、 WILLING R. I.、 SASSE W. H. F.

  DOI：——

  日期：——
• KISSANE P. J.; JOHNS S. R.; WILLING R. J.; SASSE W. H. F., AUSTRALIAN J. CHEM., 1976, 29 NO 7, 1613-1616
  作者：KISSANE P. J.、 JOHNS S. R.、 WILLING R. J.、 SASSE W. H. F.

  DOI：——

  日期：——