6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino[5,6-c]pyridin-9-ol | 1289166-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino[5,6-c]pyridin-9-ol
• 英文别名: 6,8-Bis(hydroxy-methyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino-[5,6-c]pyridin-9-ol；6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-ol
• CAS: 1289166-98-8
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: NXMSSJWYKDFXJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  92
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino[5,6-c]pyridin-9-ol 在 盐酸 作用下， 以 2,2-二甲氧基丙烷 、 丙酮 为溶剂， 反应 20.0h， 以32%的产率得到(2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5,6,8-triyl)trimethanol
  参考文献：
  名称：

  Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides

  摘要：

  Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl) pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.

  DOI：

  10.1134/s107042801101012x
• 作为产物：
  描述：

  6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate 在 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 57.0h， 生成 6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino[5,6-c]pyridin-9-ol
  参考文献：
  名称：

  Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides

  摘要：

  Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl) pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.

  DOI：

  10.1134/s107042801101012x