N-(2,3-dimethoxybenzyl)-3,4-dimethoxybenzylamine

• 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: N-(2,3-dimethoxybenzyl)-3,4-dimethoxybenzylamine
• 英文别名: 1-(3,4-dimethoxyphenyl)-N-[(2,3-dimethoxyphenyl)methyl]methanamine
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: UBEWXNWSJKFMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,3-dimethoxybenzyl)-3,4-dimethoxybenzylamine 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2,3,8,9-tetramethoxy-7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocine
  参考文献：
  名称：

  含有四环四氢异喹啉核心结构的新型取代7,12-二氢-6,12-亚甲基二苯并[c,f]偶氮辛-5-羧酸的合成

  摘要：

  开发了一种方便、简单的方案，通过三组分 Petasis 反应合成一系列新型四环四氢异喹啉衍生物 7,12-二氢-6,12-亚甲基二苯并[ c,f ]-偶氮辛-5-羧酸。使用带有取代苄基的氨基乙醛缩醛作为胺组分，然后进行 Pomeranz-Fritsch 双环化反应。通过应用该方法，已经以令人满意的收率制备了几种酸。观察到 Petasis 反应产物在稀 HCl 溶液中形成苯基甘氨酸衍生物的前所未有的化学行为，并提出了解释这种反应性的机制。

  DOI：

  10.3762/bjoc.17.168
• 作为产物：
  描述：

  在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 N-(2,3-dimethoxybenzyl)-3,4-dimethoxybenzylamine
  参考文献：
  名称：

  Synthesis of 7,12-Dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-Dibenzylphenacylamines

  摘要：

  N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-l2-phenyl-5H-6,1 2-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cycIization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid al room temperature.

  DOI：

  10.3987/com-97-7986

文献信息

• Synthesis of 7,12-Dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-Dibenzylphenacylamines
  作者：Necdet Coskun、Necdet Coskun、Levent Büyükuysal

  DOI：10.3987/com-97-7986

  日期：——

  N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-l2-phenyl-5H-6,1 2-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cycIization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid al room temperature.
• Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[<i>c,f</i>]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure
  作者：Agnieszka Grajewska、Maria Chrzanowska、Wiktoria Adamska

  DOI：10.3762/bjoc.17.168

  日期：——

  A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying

  开发了一种方便、简单的方案，通过三组分 Petasis 反应合成一系列新型四环四氢异喹啉衍生物 7,12-二氢-6,12-亚甲基二苯并[ c,f ]-偶氮辛-5-羧酸。使用带有取代苄基的氨基乙醛缩醛作为胺组分，然后进行 Pomeranz-Fritsch 双环化反应。通过应用该方法，已经以令人满意的收率制备了几种酸。观察到 Petasis 反应产物在稀 HCl 溶液中形成苯基甘氨酸衍生物的前所未有的化学行为，并提出了解释这种反应性的机制。