1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione | 1432067-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione
• 英文别名: 1-Hydroxy-8-(2-phenylselanylethoxy)anthracene-9,10-dione
• CAS: 1432067-84-9
• 化学式: C₂₂H₁₆O₄Se
• 分子量: 423.327
• InChiKey: OTSVMZWQYBOUBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione 在 iron perchlorate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione
  参考文献：
  名称：

  Synthesis, reactivity, catenation and X-ray crystallography of Ag+ and Cu+ complexes of anthraquinone-based selenoethers: A luminescent chemodosimeter for Cu2+ and Fe3+

  摘要：

  Reaction of the PhSe- anion with 1,8-bis(2-bromoethoxy)anthracene-9,10-dione, 1,5-bis(2-bromoethoxy)anthracene-9,10-dione, 1,8-bis(2-bromoethylethyleneoxy)anthracene-9,10-dione in 1:1 ratio generates 1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione (2), 1,5-bis(2-phenylselenoethoxy) anthracene-9,10-dione (3) and 1,8-bis(2-phenylselenoethylethyleneoxy)anthracene-9,10-dione (4). The reaction of 2 with a methanolic solution of Ag(CH3CN)(4)BF4 and Cu(CH3CN)(4)BF4, yielded metal complexes 5 and 6, respectively. 3 formed a ID coordination polymer (7) with Ag(CH3CN)(4)BF4 in a 1:2 ratio. The anthraquinone in 3 exhibits pi-pi interactions with distances in a range of 3.512-3.840 angstrom. 2 acts as a chemodosimeter for Cu2+ and Fe3+ as it undergoes an aryl ether cleavage with Cu2+ and Fe3+ and produces the luminescent 1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione (8). Intramolecular hydrogen bonding in 8 is responsible for the red-orange (lambda(max) 595 nm) emission. The X-ray structures of 5, 6, 7, and 8 are reported along with cyclic voltammetric analyses of new organoselenium compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.03.003