[2-(1,3-Benzothiazol-2-yl)-6-methoxyphenyl] 2-[[2-[2-(1,3-benzothiazol-2-yl)-6-methoxyphenoxy]carbonylphenyl]disulfanyl]benzoate | 1478061-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: [2-(1,3-Benzothiazol-2-yl)-6-methoxyphenyl] 2-[[2-[2-(1,3-benzothiazol-2-yl)-6-methoxyphenoxy]carbonylphenyl]disulfanyl]benzoate
• CAS: 1478061-65-2
• 化学式: C₄₂H₂₈N₂O₆S₄
• 分子量: 784.958
• InChiKey: XQAJQLMGGQIMAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  204
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2, 2'-二硫代二苯甲酸 、 2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到[2-(1,3-Benzothiazol-2-yl)-6-methoxyphenyl] 2-[[2-[2-(1,3-benzothiazol-2-yl)-6-methoxyphenoxy]carbonylphenyl]disulfanyl]benzoate
  参考文献：
  名称：

  A ratiometric fluorescent probe for hydrogen sulfide based on an excited-state intramolecular proton transfer mechanism

  摘要：

  A ratiometric fluorescent probe for hydrogen sulfide (H2S) has been developed based on modulation of the excited-state intramolecular proton transfer (ESIPT) process of 2-(2'-hydroxy-3'-methoxyphenyl) benzothiazole (HMBT). The probe was prepared by coupling HMBT with 3,3'-dithiodipropionic acid, and it only displays enol-like fluorescence emission at 374 nm. However, upon introducing H2S in neutral solution, the protecting groups of the probe was removed via the tandem nucleophilic substitution/cyclization reaction, thereby retrieving the ESIPT process of HMBT, which resulted in a decrease of the emission band at 374 nm along with a concomitant increase of a new fluorescence peak at 478 nm. The fluorescent intensity ratio at 478 and 374 nm (I-478/I-374) increases linearly with H2S concentration in the range 0.5-10 mu M. The proposed probe shows excellent selectivity toward H2S over other common anions and biothiols. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.033