3',6'-二羟基-3H-螺[2-苯并呋喃-1,9'-噻吨]-3-酮 | 94109-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 中文名称: 3',6'-二羟基-3H-螺[2-苯并呋喃-1,9'-噻吨]-3-酮
• 中文别名: 5-(1-羟基己基)二氢呋喃-2(3H)-酮
• 英文名称: 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-[9H]thioxanthen]-3-one
• 英文别名: thiofluorescein；spiro[isobenzofuran-3',6'-dihydroxy-1(3H),9'-[9H]thioxanthen]-3-one；3',6'-dihydroxy-spiro[phthalan-1,9'-thioxanthen]-3-one；3',6'-Dihydroxy-spiro[phthalan-1,9'-thioxanthen]-3-on；3',6'-dihydroxyspiro(isobenzofuran-1(3H),9'-[9H]thioxanthene)-3-one；3',6'-Dihydroxyspiro(isobenzofuran-1(3H),9'-(9H)thioxanthene)-3-one；3',6'-dihydroxyspiro[2-benzofuran-3,9'-thioxanthene]-1-one
• CAS: 94109-78-1
• 化学式: C₂₀H₁₂O₄S
• 分子量: 348.379
• InChiKey: PTTMNOGNUQNMFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3',6'-二羟基-3H-螺[2-苯并呋喃-1,9'-噻吨]-3-酮 生成 阿司匹林杂质G
  参考文献：
  名称：

  Meyer,R., Chemische Berichte, 1900, vol. 33, p. 2571

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(3-methoxyphenyl)sulfide 在 硫酸 、 吡啶盐酸盐 作用下， 反应 1.5h， 生成 3',6'-二羟基-3H-螺[2-苯并呋喃-1,9'-噻吨]-3-酮
  参考文献：
  名称：

  Improved Synthesis of Thiofluorescein

  摘要：

  通过将 3,3′-二甲氧基二苯硫醚连续去甲基化为 3,3′-二羟基二苯硫醚，并将后者与邻苯二甲酸酐在 H2SO4 中缩合，以制备收率合成了硫荧光素。通过在 H2SO4 中缩合和在 2 Py - H2SO4 中去甲基化的单锅工艺，还可以直接从 3,3′-二甲氧基二苯硫醚中获得产率更高的标题化合物。

  DOI：

  10.1007/s11178-005-0120-3

文献信息

• Meyer,R.; Szanecki, Chemische Berichte, 1900, vol. 33, p. 2579
  作者：Meyer,R.、Szanecki

  DOI：——

  日期：——
• Development of a Selective Fluorescent Probe for Hypochlorous Acid Detection and Imaging
  作者：Qingling Xu、Min Jeong Choi、Gyoungmi Kim、Sang‐Hyup Lee、Juyoung Yoon

  DOI：10.1002/bkcs.11614

  日期：2018.12
• Wyler, Dissertation <Zuerich 1894>, S. 12
  作者：Wyler

  DOI：——

  日期：——
• Brominated and iodinated thiofluoresceins
  作者：V. V. Russkikh、E. V. Vasil’ev、V. V. Shelkovnikov

  DOI：10.1134/s1070428008100242

  日期：2008.10

  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.
• ——
  作者：N. O. Mchedlov-Petrosyan、N. A. Vodolazkaya、V. P. Martynova、D. V. Samoilov、A. V. El'tsov

  DOI：10.1023/a:1019524722318

  日期：——

  Ionization constants of thiofluorescein, 4-nitro-, 4,5-dinitro-, 2,4,5,7-tetrabromo-, and 2,4,5,7-tetra-iodothiofluoresceins, and also of 4,5-dibromofluorescein and N-ethyl-4,5-dinitroazafluorescein in 50 wt % aqueous ethanol have been determined. The electronic absorption spectra of their ionic and molecular forms have been recorded and analyzed. The behavior of these dyes can be described in terms of the scheme of prototropic equilibria proposed previously for fluorescein and its halo derivatives.