Methanesulfonic acid 6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester | 215595-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid 6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester
• CAS: 215595-85-0
• 化学式: C₁₂H₁₆FNO₅S
• 分子量: 305.327
• InChiKey: NUGLNFOIZXCZBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.72
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以74%的产率得到5-Azidomethyl-6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine
  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：

  6-amino-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol 在 4-二甲氨基吡啶 、 氢氟酸 、 对甲苯磺酸 、 三乙胺 、 sodium nitrite 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 Methanesulfonic acid 6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl 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