6-Fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid methyl ester | 215595-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid methyl ester
• CAS: 215595-91-8
• 化学式: C₁₂H₁₄FNO₄
• 分子量: 255.246
• InChiKey: HDDUQFKUGQRDOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.65
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-Fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid methyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以85%的产率得到4-Fluoro-7-hydroxy-6-methyl-1H-furo[3,4-c]pyridin-3-one
  参考文献：
  名称：

  Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues

  摘要：

  We have synthesized a series of novel fluorinated vitamin B-6 analogues (6-fluoropyridoxol derivatives) as potential F-19 NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4- or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid-base titration showed pK(a) values in the range 7.05-9.5 with a chemical shift sensitivity in the range 7.4-12 ppm. Several of the molecules readily cross cell membranes providing estimates of both intra- and extra-cellular pH in whole blood. 6-Fluoropyridoxamine (6-FPAM) exhibits a pK(a) = 7.05, which is closer to normal physiological pH than the parent molecule 6-fluoropyridoxol (6-FPOL) (pK(a) = 8.2), and should thus, be useful for precise and accurate measurements of pH in vivo. Enhanced spectral resolution for 6-FPAM over 6-FPOL is demonstrated in whole blood and the perfused rat heart. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00104-7
• 作为产物：
  描述：

  甲醇 、 6-Fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carbaldehyde 在 manganese(IV) oxide 、 溶剂黄146 作用下， 反应 12.0h， 以71%的产率得到6-Fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues

  摘要：

  We have synthesized a series of novel fluorinated vitamin B-6 analogues (6-fluoropyridoxol derivatives) as potential F-19 NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4- or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid-base titration showed pK(a) values in the range 7.05-9.5 with a chemical shift sensitivity in the range 7.4-12 ppm. Several of the molecules readily cross cell membranes providing estimates of both intra- and extra-cellular pH in whole blood. 6-Fluoropyridoxamine (6-FPAM) exhibits a pK(a) = 7.05, which is closer to normal physiological pH than the parent molecule 6-fluoropyridoxol (6-FPOL) (pK(a) = 8.2), and should thus, be useful for precise and accurate measurements of pH in vivo. Enhanced spectral resolution for 6-FPAM over 6-FPOL is demonstrated in whole blood and the perfused rat heart. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00104-7