9-(4-methoxy-2-methylphenyl)-3-oxo-3H-xanthen-6-yl acetate | 1326231-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(4-methoxy-2-methylphenyl)-3-oxo-3H-xanthen-6-yl acetate
• CAS: 1326231-92-8
• 化学式: C₂₃H₁₈O₅
• 分子量: 374.393
• InChiKey: SRABUKFTOKUOFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Tokyo green 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以34%的产率得到9-(4-methoxy-2-methylphenyl)-3-oxo-3H-xanthen-6-yl acetate
  参考文献：
  名称：

  β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold

  摘要：

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.

  DOI：

  10.1021/ja204781t