3,5-dibenzyloxy-6-benzyloxymethyl-2-pyridone | 1438996-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dibenzyloxy-6-benzyloxymethyl-2-pyridone
• 英文别名: 3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-1H-pyridin-2-one
• CAS: 1438996-96-3
• 化学式: C₂₇H₂₅NO₄
• 分子量: 427.5
• InChiKey: NEZHZIXRXMQMQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dibenzyloxy-6-benzyloxymethyl-2-pyridone 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-O-decyl-3,5-dihydroxy-6-methylpyridine
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083
• 作为产物：
  描述：

  5-hydroxy-2,3,4,6-tetra-O-benzyl-δ-lactam 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以70%的产率得到3,5-dibenzyloxy-6-benzyloxymethyl-2-pyridone
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083

文献信息

• An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate
  作者：Jaggaiah N. Gorantla、Divya Kovval、Ravi S. Lankalapalli

  DOI：10.1016/j.tetlet.2013.03.083

  日期：2013.6

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.