[D,13C]-4-hydroxybenzaldehyde 4-methylbenzenesulfonate ester | 1440912-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [D,13C]-4-hydroxybenzaldehyde 4-methylbenzenesulfonate ester
• 英文别名: [D,¹³C]-4-hydroxybenzaldehyde 4-methylbenzenesulfonate ester
• CAS: 1440912-94-6
• 化学式: C₁₄H₁₂O₄S
• 分子量: 278.294
• InChiKey: UPOKXWYTSBUETD-HDGSCLRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  9-甲基-9H-芴-9-羰基-13C氯化物 、 4-甲基苯磺酸-4-碘苯酯 在 dichloro(cycloocta-1,5-diene)palladium (II) 、 N-甲基二环己基胺 、 四丁基碘化铵 、 potassium deuteroformate 、 tricyclohexylphosphine tetrafluoroborate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以80%的产率得到[D,13C]-4-hydroxybenzaldehyde 4-methylbenzenesulfonate ester
  参考文献：
  名称：

  Reductive Carbonylation of Aryl Halides Employing a Two-Chamber Reactor: A Protocol for the Synthesis of Aryl Aldehydes Including ¹³C- and D-Isotope Labeling

  摘要：

  A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9-carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number Of functional groups positioned on the aromatic ring, and it can be exploited for the isotope labeling of the aldehyde group. Hence, reductive carbonylations run with (13)COgen provide a facile access to C-13-labeled aromatic aldehydes, whereas with DCO2K, the aldehyde is specifically labeled with deuterium. Two examples of double isotopic labeling are also demonstrated. Finally, the method was applied to the specific carbon-13 labeling of the beta-amyloid binding compound, florbetaben.

  DOI：

  10.1021/jo400741t