5-(hydroxymethyl)-2-methyl-4-((tert-pentyloxy)methyl)pyridin-3-ol

• 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: 5-(hydroxymethyl)-2-methyl-4-((tert-pentyloxy)methyl)pyridin-3-ol
• 英文别名: 5-(Hydroxymethyl)-2-methyl-4-(2-methylbutan-2-yloxymethyl)pyridin-3-ol；5-(hydroxymethyl)-2-methyl-4-(2-methylbutan-2-yloxymethyl)pyridin-3-ol
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: UEUVSRDOMCKHFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-2-丁醇 、 2-甲基-3-羟基-4,5-二羟甲基吡啶 以 neat (no solvent) 为溶剂， 反应 96.0h， 以50%的产率得到5-(hydroxymethyl)-2-methyl-4-((tert-pentyloxy)methyl)pyridin-3-ol
  参考文献：
  名称：

  A regioselective etherification of pyridoxine via an ortho -pyridinone methide intermediate

  摘要：

  The catalyst-free, regioselective synthesis of 4'-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the ortho-pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.04.082

文献信息

• A regioselective etherification of pyridoxine via an ortho -pyridinone methide intermediate
  作者：Jessica A. Yazarians、Brian L. Jiménez、Gregory R. Boyce

  DOI：10.1016/j.tetlet.2017.04.082

  日期：2017.6

  The catalyst-free, regioselective synthesis of 4'-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the ortho-pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols. (C) 2017 Elsevier Ltd. All rights reserved.