3,3,5,9,9-pentamethyl-7,11-dihydro-1H-[1,3]dioxepino[5,6-b][1,3]dioxino-[5,4-d]pyridine | 1243585-31-0

• 分子结构分类: 有机化合物
• 英文名称: 3,3,5,9,9-pentamethyl-7,11-dihydro-1H-[1,3]dioxepino[5,6-b][1,3]dioxino-[5,4-d]pyridine
• 英文别名: 3,3,5,9,9-Pentamethyl-7,11-dihydro-1h-[1,3]di-oxepino[5,6-b][1,3]dioxino[5,4-d]pyridine；5,5,8,13,13-pentamethyl-4,6,12,14-tetraoxa-9-azatricyclo[8.5.0.02,7]pentadeca-1,7,9-triene
• CAS: 1243585-31-0
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: MRPGJPDIVQGNAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3,5,9,9-pentamethyl-7,11-dihydro-1H-[1,3]dioxepino[5,6-b][1,3]dioxino-[5,4-d]pyridine 在 乙醇 、 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 52.0h， 生成 3,3,9,9-tetramethyl-7,11-dihydro-1H-[1,3]dioxepino[5,6-b][1,3]dioxino[5,4-d]pyridin-5-ylmethanol
  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-(hydroxymethyl)-3,3,8-trimethyl-1,5-dihydro-[1,3] dioxepino [5,6-c] pyridin-9-ol 在 盐酸 、 2,2-二甲氧基丙烷 作用下， 反应 50.0h， 生成 3,3,5,9,9-pentamethyl-7,11-dihydro-1H-[1,3]dioxepino[5,6-b][1,3]dioxino-[5,4-d]pyridine
  参考文献：
  名称：

  基于吡ido醇的新型phospho盐的合成及抑菌活性

  摘要：

  在吡x嗪衍生物的基础上合成了13种phospho盐，并在体外测试了它们对临床相关菌株的抗菌活性。所有化合物对革兰氏阴性菌几乎没有活性，对革兰氏阳性菌表现出结构依赖性活性。已证明了缩酮保护基在phospho盐中的抗菌特性至关重要。在合成的化合物中，发现5,6-双[三苯基膦基（甲基）]-2,2,8-三甲基-4 H- [1,3]二氧杂[4,5- c ]吡啶二氯化物（化合物20）是对金黄色葡萄球菌和表皮葡萄球菌最有效菌株（MIC 5μg/ ml）。该化合物的抗菌活性机制可能涉及细胞渗透以及与基因组和质粒DNA的相互作用。

  DOI：

  10.1016/j.bmc.2013.04.051

文献信息

• Theoretical and experimental study on cyclic 6-methyl-2,3,4-tris(hydroxymethyl)pyridin-5-ol acetonides
  作者：N. V. Shtyrlin、O. A. Lodochnikova、M. V. Pugachev、T. I. Madzhidov、L. P. Sysoeva、I. A. Litvinov、E. N. Klimovitskii、Yu. G. Shtyrlin

  DOI：10.1134/s1070428010040202

  日期：2010.4

  Methods for the preparation of three cyclic 2,3,4-tris(hydroxymethyl)-6-methylpyridin-5-ol acetonides have been developed by variation of the reaction conditions. The six-membered acetonide turned out to be thermodynamically more stable than the seven-membered acetonide and bis-acetonide. The experimental data were consistent with the results of quantum-chemical calculations. The structure of the isolated compounds was proved by X-ray analysis.