(E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-methoxystyryl)benzene | 1379597-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-methoxystyryl)benzene
• CAS: 1379597-73-5
• 化学式: C₂₈H₂₅FO₆
• 分子量: 478.479
• InChiKey: YWWHSEDUHMWZNA-QZMBWGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-methoxystyryl)benzene 在 水 、 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-hydroxystyryl)benzene
  参考文献：
  名称：

  Isotope-Labeling of the Fibril Binding Compound FSB via a Pd-Catalyzed Double Alkoxycarbonylation

  摘要：

  We have synthesized two isotopically labeled variants of the beta-amyloid binding compound FSB possessing C-13-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The C-13-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated C-13-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.

  DOI：

  10.1021/jo300746x
• 作为产物：
  描述：

  4,4'-((2-fluoro-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-chloro-1-methoxybenzene) 在 bis(η3-allyl-μ-chloropalladium(II)) 、 dicyclohexyl(3-dicyclohexylphosphaniumylpropyl)phosphonium ditetrafluoroborate 、 六甲基二硅烷 、 水 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 (E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-methoxystyryl)benzene
  参考文献：
  名称：

  Isotope-Labeling of the Fibril Binding Compound FSB via a Pd-Catalyzed Double Alkoxycarbonylation

  摘要：

  We have synthesized two isotopically labeled variants of the beta-amyloid binding compound FSB possessing C-13-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The C-13-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated C-13-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.

  DOI：

  10.1021/jo300746x