(6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methanol | 215595-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methanol
• 英文别名: (6-Fluoro-2,2,8-trimethyl-2H,4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol；(6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol
• CAS: 215595-84-9
• 化学式: C₁₁H₁₄FNO₃
• 分子量: 227.235
• InChiKey: BAPQNRKHDZSBQX-UHFFFAOYSA-N

物化性质

• 沸点：
  340.0±42.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methanol 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 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 氢氟酸 、 对甲苯磺酸 、 sodium nitrite 作用下， 以 吡啶 为溶剂， 反应 26.5h， 生成 (6-fluoro-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methanol
  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

文献信息

• Chemistry and biology of vitamin B6. 31. Synthesis and physicochemical and biological properties of 6-halogen-substituted vitamin B6 analogs
  作者：W. Korytnyk、S. C. Srivastava

  DOI：10.1021/jm00264a013

  日期：1973.6
• Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues
  作者：Sha He、Ralph P. Mason、Sandeep Hunjan、Vimal D. Mehta、Veera Arora、Revathi Katipally、Padmakar V. Kulkarni、Peter P. Antich

  DOI：10.1016/s0968-0896(98)00104-7

  日期：1998.9

  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.