2',4'-5'-tribromo-3',6'-dihydroxyspiro[2-benzofuran-1,9'-thioxanthen]-3-one | 1186088-39-0

• 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: 2',4'-5'-tribromo-3',6'-dihydroxyspiro[2-benzofuran-1,9'-thioxanthen]-3-one
• CAS: 1186088-39-0
• 化学式: C₂₀H₉Br₃O₄S
• 分子量: 585.067
• InChiKey: KYDVFYBBSQEVAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3',6'-二羟基-3H-螺[2-苯并呋喃-1,9'-噻吨]-3-酮 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 反应 2.0h， 以73%的产率得到2',4'-5',7'-tetrabromo-3',6'-dihydroxyspiro[2-benzofuran-1,9'-thioxanthen]-3-one
  参考文献：
  名称：

  Brominated and iodinated thiofluoresceins

  摘要：

  Conditions were found for the synthesis of mono-, di-, tri-, and tetrabromo- and -iodo-substituted thiofluoresceins. Iodination and bromination of thiofluorescein with molecular iodine and bromine in 1 N aqueous sodium hydroxide gave mixtures of the corresponding 2,4,5,7-tetra- and 2,4,5-trihalo derivatives in 71/14 (Y = I) and 73/13% yield (Y = Br), respectively. In the reactions of thiofluorescein with bromine in acetic acid and with iodine in methanol at a substrate-to-halogen ratio of 1 : 2, 4,5-dibromo- and 4,5-diiodothiofluoresceins were isolated in 56 and 67% yield. Analogous reactions with equimolar amounts of the reactants produced 59% of 4-bromothiofluorescein and 51% of 4-iodothiofluorescein.

  DOI：

  10.1134/s1070428008100242