methanesulfonic acid 2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)ethyl ester | 1084890-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methanesulfonic acid 2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)ethyl ester
• 英文别名: 2-[(9,10-Dioxoanthracen-1-yl)amino]ethyl methanesulfonate；2-[(9,10-dioxoanthracen-1-yl)amino]ethyl methanesulfonate
• CAS: 1084890-33-4
• 化学式: C₁₇H₁₅NO₅S
• 分子量: 345.376
• InChiKey: BETOVTDNMGGCAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)ethyl ester 在 sodium azide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1-[(2-azidoethyl)amino]anthracene-9,10-dione
  参考文献：
  名称：

  WO2008/144472

  摘要：

  公开号：
• 作为产物：
  描述：

  溶剂红L-B 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到methanesulfonic acid 2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)ethyl ester
  参考文献：
  名称：

  1-Aminoanthracene-9,10-dione based chromogenic molecular sensors: effect of nature and number of nitrogen atoms on metal ion sensing behavior

  摘要：

  To examine the consequences of nature and number of nitrogen atoms on metal ion sensing properties, four new molecular receptors based on 1-aminoanthracene-9,10-dione as chromogenic moiety and different types of nitrogen atoms viz. arylamine, alkylamine, and pyridyl nitrogen as appendages have been synthesized. These receptors in CH(3)OH/H(2)O (1:1) (v/v) at pH 7.0, on addition of heavy metal ions show selective and/or semi-selective interactions. These binding interactions are visible to naked eye due to remarkable color change and are associated with lambda(max) shift by 85-125 nm. Molecular receptor 2, with two sp(2) hybridized nitrogen atoms and one arylamine nitrogen, selectively binds with Cu(2+) but 2-Cu(2+) complex is stable only between pH 7.0 and 8.75. However, the conversion of imine nitrogen to alkylamine in molecular receptor 6, increases the binding ability toward Cu(2+) along with significant binding affinities toward Ni(2+) and Co(2+). Receptor 6 shows the stability of its complexes in the order Cu(2+)>Ni(2+)>Co(2+) in a broader pH range 6-12. Dipicolylamine based receptor 8, possessing two pyridyl nitrogen atoms, one tertiaryamine and one arylamine nitrogen atoms as ligating sites, also binds semiselectively in the order Cu(2+)>Co(2+)>Ni(2+). Receptor 10, possessing anilide group in the place of arylamine in receptor 8, on addition of Cu(2+), Ni(2+) or Co(2+) shows bathochromic shift of lambda(max) associated with color change from yellow to russet (brown) and on addition of Zn(2+) shows hypsochromic shift of its lambda(max) associated with disappearance of yellow color. Additionally, all the four chemosensors show ratiometric response toward all these metal ions and thus increase the usability and the dynamic range of estimation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.031

文献信息

• WO2008/144472
  申请人：——

  公开号：——

  公开（公告）日：——
• 1-Aminoanthracene-9,10-dione based chromogenic molecular sensors: effect of nature and number of nitrogen atoms on metal ion sensing behavior
  作者：Kuljit Kaur、Subodh Kumar

  DOI：10.1016/j.tet.2010.06.031

  日期：2010.8

  To examine the consequences of nature and number of nitrogen atoms on metal ion sensing properties, four new molecular receptors based on 1-aminoanthracene-9,10-dione as chromogenic moiety and different types of nitrogen atoms viz. arylamine, alkylamine, and pyridyl nitrogen as appendages have been synthesized. These receptors in CH(3)OH/H(2)O (1:1) (v/v) at pH 7.0, on addition of heavy metal ions show selective and/or semi-selective interactions. These binding interactions are visible to naked eye due to remarkable color change and are associated with lambda(max) shift by 85-125 nm. Molecular receptor 2, with two sp(2) hybridized nitrogen atoms and one arylamine nitrogen, selectively binds with Cu(2+) but 2-Cu(2+) complex is stable only between pH 7.0 and 8.75. However, the conversion of imine nitrogen to alkylamine in molecular receptor 6, increases the binding ability toward Cu(2+) along with significant binding affinities toward Ni(2+) and Co(2+). Receptor 6 shows the stability of its complexes in the order Cu(2+)>Ni(2+)>Co(2+) in a broader pH range 6-12. Dipicolylamine based receptor 8, possessing two pyridyl nitrogen atoms, one tertiaryamine and one arylamine nitrogen atoms as ligating sites, also binds semiselectively in the order Cu(2+)>Co(2+)>Ni(2+). Receptor 10, possessing anilide group in the place of arylamine in receptor 8, on addition of Cu(2+), Ni(2+) or Co(2+) shows bathochromic shift of lambda(max) associated with color change from yellow to russet (brown) and on addition of Zn(2+) shows hypsochromic shift of its lambda(max) associated with disappearance of yellow color. Additionally, all the four chemosensors show ratiometric response toward all these metal ions and thus increase the usability and the dynamic range of estimation. (C) 2010 Elsevier Ltd. All rights reserved.