5-fluoronorepinephrine | 71144-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-fluoronorepinephrine
• 英文别名: Benzeneethanamine, 3-fluoro-beta,4,5-trihydroxy-；5-(2-amino-1-hydroxyethyl)-3-fluorobenzene-1,2-diol
• CAS: 71144-41-7
• 化学式: C₈H₁₀FNO₃
• 分子量: 187.171
• InChiKey: CMXBGHSRBYAOPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-fluoronorepinephrine 在 sodium periodate 、 S-腺苷L-甲硫氨酸 、 Tris buffer 、 S-腺苷基-L-蛋氨碘盐 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 为溶剂， 生成 3-氟-4-羟基-5-甲氧基苯甲醛 、 3-fluoro-4-methoxy-5-hydroxybenzaldehyde
  参考文献：
  名称：

  Influence of fluorine substitution on the site of enzymic O-methylation of fluorinated norepinephrines

  摘要：

  The extent of meta- and para-O-methylation by catechol O-methyltransferase of 2-fluoro-, 5-fluoro-, and 6-fluoronorepinephrine (FNE) at pH 7 and 9 was determined. The rank order of preference for para-O-methylation is 5FNE much greater than NE greater than 6FNE greater than 2FNE. In all cases, increasing the pH to 9 results in an increase in para-O-methylation. Results with 2F- and 5FNE demonstrate the importance of ionization in the methyltransferase reaction when fluorine is situated ortho to one of the phenolic groups. To establish unequivocally the identities of the products, the isomeric, monofluorinated vanillins and isovanillins were synthesized and directly related to the products formed enzymatically from the monofluorinated norepinephrines.

  DOI：

  10.1021/jm00144a005

文献信息

• Influence of fluorine substitution on the site of enzymic O-methylation of fluorinated norepinephrines
  作者：Cyrus R. Creveling、Elizabeth T. McNeal、Daniele Cantacuzene、Kenneth L. Kirk

  DOI：10.1021/jm00144a005

  日期：1981.12

  The extent of meta- and para-O-methylation by catechol O-methyltransferase of 2-fluoro-, 5-fluoro-, and 6-fluoronorepinephrine (FNE) at pH 7 and 9 was determined. The rank order of preference for para-O-methylation is 5FNE much greater than NE greater than 6FNE greater than 2FNE. In all cases, increasing the pH to 9 results in an increase in para-O-methylation. Results with 2F- and 5FNE demonstrate the importance of ionization in the methyltransferase reaction when fluorine is situated ortho to one of the phenolic groups. To establish unequivocally the identities of the products, the isomeric, monofluorinated vanillins and isovanillins were synthesized and directly related to the products formed enzymatically from the monofluorinated norepinephrines.