6-methoxy-4-methyl-2,3-dihydrofuro[2,3-b]pyridine-5-carbonitrile | 32383-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methoxy-4-methyl-2,3-dihydrofuro[2,3-b]pyridine-5-carbonitrile
• 英文别名: 5-Cyano-2,3-dihydro-6-methoxy-4-methylfuro<2,3-b>pyridin
• CAS: 32383-16-7
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: WHDBKPOKNUTJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原甲酸三甲酯 、 2,6-dihydroxy-5-(2-hydroxy-ethyl)-4-methyl-nicotinonitrile 在 Montmorillonite K₁₀ 作用下， 反应 48.0h， 以14%的产率得到3-cyano-2-methoxy-5-(2-methoxyethyl)-4-methylpyridin-6-one
  参考文献：
  名称：

  On the methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones

  摘要：

  In order to prepare new heterocyclic derivatives as building block for compounds with potential biological activities, we were led to study the O-methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones such as 1. This enabled us to develop a new two steps method to prepare the corresponding 2,6-dimethoxy derivative 5 in 80 % yield. It consisted first in heating 1 in trimethylorthoformate, with or without an acidic catalyst, which gave a mixture of the two mono-methoxy isomers, then a classical methylation of the second hydroxy moiety led almost exclusively to 5. In this paper we present this "methylation" method and various unexpected results recorded when we attempted to extend it to related derivatives or to other heterocycle containing lactim-lactam functions. An intramolecular transetherification mechanism requiring the simultaneous transfer of a hydrogen and a methyl is suggested. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00755-3

文献信息

• On the methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones
  作者：Yves Louis Janin、Jaouad Chiki、Michel Legraverend、Christiane Huel、Emile Bisagni

  DOI：10.1016/s0040-4020(99)00755-3

  日期：1999.10

  In order to prepare new heterocyclic derivatives as building block for compounds with potential biological activities, we were led to study the O-methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones such as 1. This enabled us to develop a new two steps method to prepare the corresponding 2,6-dimethoxy derivative 5 in 80 % yield. It consisted first in heating 1 in trimethylorthoformate, with or without an acidic catalyst, which gave a mixture of the two mono-methoxy isomers, then a classical methylation of the second hydroxy moiety led almost exclusively to 5. In this paper we present this "methylation" method and various unexpected results recorded when we attempted to extend it to related derivatives or to other heterocycle containing lactim-lactam functions. An intramolecular transetherification mechanism requiring the simultaneous transfer of a hydrogen and a methyl is suggested. (C) 1999 Elsevier Science Ltd. All rights reserved.

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