3,3-双(3-氟-4-羟基苯基)-2-苯并呋喃-1-酮 | 90278-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3,3-双(3-氟-4-羟基苯基)-2-苯并呋喃-1-酮
• 英文名称: 3,3-bis(3-fluoro-4-hydroxyphenyl)isobenzofuran-1(3H)-one
• 英文别名: 3,3-Bis(3-fluoro-4-hydroxyphenyl)-2-benzofuran-1(3H)-one；3,3-bis(3-fluoro-4-hydroxyphenyl)-2-benzofuran-1-one
• CAS: 90278-65-2
• 化学式: C₂₀H₁₂F₂O₄
• 分子量: 354.31
• InChiKey: INZKIQVIOKYBJN-UHFFFAOYSA-N

物化性质

• 沸点：
  535.7±50.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  酚酞 在 fluorine 、 三氟乙酸 作用下， 反应 0.08h， 生成 (RS)-3-(3-fluoro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-one 、 3,3-双(3-氟-4-羟基苯基)-2-苯并呋喃-1-酮
  参考文献：
  名称：

  Synthesis of 18F-labeled phenolphthalein and naphtholphthalein

  摘要：

  The fluorination of phenolphthalein and naphtholphthalein was performed with diluted fluorine gas under acidic conditions. For both compounds we observed an electrophilic fluorination into ortho position to the hydroxyl group. Through the use of this reaction we synthesized and characterized mono- and difluorinated derivatives of phenolphthalein and naphtholphthalein. The compounds were also prepared in the F-18 labeled form, which are usable as a new type of probe for in vivo pH measurement in biological objects using Cerenkov imaging or combination of light absorption and PET. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.03.021

文献信息

• FLUORINE-18 LABELED HYDROGEN ION PROBES
  申请人：The Trustees of The University of Pennsylvania

  公开号：US20140369933A1

  公开（公告）日：2014-12-18

  Fluorine-containing molecules include fluorine-18 labeled hydrogen ion indicator molecules and methods of making and using the same. Fluorine atoms incorporated into the indicator molecules provides novel structural modifications to the precursor molecules, shifting the absorbance maxima relative to their non-fluorinated precursor/cogeners. These molecules are useful for non-invasive in vivo measurement of blood volume, blood flow and pH in biological objects. Compounds are functionalized by a radioisotopically enriched fluorine-18 label and indicator molecule with structure derived from triarylmethane derived indicators, such as phenol red, cresol red, cresol purple, thymol blue, bromophenol red, naphthol blue, phenolphthalein, cresolphthalein, thymolphthalein, naphtholphthalein, gentian violet (methyl violet 10B), methyl violet 2B, methyl violet 6B, leucomalachite green (malachite green), brilliant green, pararosaniline, fuchsines, or salts thereof. During its radioactive decay, fluorine-18 produces high-energy positrons, which can be detected by positron emission tomography (PET) or single photon emission computer tomography (SPECT).

  含氟分子包括氟-18标记的氢离子指示分子及其制备和使用方法。将氟原子纳入指示分子中，可对前体分子进行新颖的结构修饰，使吸收峰相对于非氟化前体/同系物发生位移。这些分子对于生物对象的无创体内测量血容量、血流和pH值非常有用。化合物通过放射性同位素富集的氟-18标记进行官能化，并且指示分子的结构来源于三芳基甲烷衍生指示剂，例如酚红、甲酚红、甲酚紫、百里酚蓝、溴酚红、萘酚蓝、酚酞、甲酚酞、百里酚酞、萘酚酞、龙胆紫（甲基紫10B）、甲基紫2B、甲基紫6B、亚甲基绿（孔雀绿）、亮绿、对苯偶氮苯胺、品红或其盐。在其放射性衰变过程中，氟-18会产生高能正电子，可以通过正电子发射断层扫描（PET）或单光子发射计算机断层扫描（SPECT）进行检测。
• Synthesis of 18F-labeled phenolphthalein and naphtholphthalein
  作者：Alexander V. Kachur、Andrey A. Popov、E. James Delikatny、Joel S. Karp、Anatoliy V. Popov

  DOI：10.1016/j.jfluchem.2013.03.021

  日期：2013.7

  The fluorination of phenolphthalein and naphtholphthalein was performed with diluted fluorine gas under acidic conditions. For both compounds we observed an electrophilic fluorination into ortho position to the hydroxyl group. Through the use of this reaction we synthesized and characterized mono- and difluorinated derivatives of phenolphthalein and naphtholphthalein. The compounds were also prepared in the F-18 labeled form, which are usable as a new type of probe for in vivo pH measurement in biological objects using Cerenkov imaging or combination of light absorption and PET. (c) 2013 Elsevier B.V. All rights reserved.