N-(2,4-dimethoxybenzyl)-2-hydroxybenzamide

• 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-(2,4-dimethoxybenzyl)-2-hydroxybenzamide
• 英文别名: N-[(2,4-dimethoxyphenyl)methyl]-2-hydroxybenzamide
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: BCYLADTVYWABJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,4-dimethoxybenzyl)-2-hydroxybenzamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到水杨酰胺
  参考文献：
  名称：

  Selective N-debenzylation of amides with p-TsOH

  摘要：

  N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxyl-benzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02738-7
• 作为产物：
  描述：

  2,4-二甲氧基苯甲胺 、 水杨酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到N-(2,4-dimethoxybenzyl)-2-hydroxybenzamide
  参考文献：
  名称：

  丁二烯[1.4]奥氮平的水合咪唑啉环扩展（HIRE）的替代方法

  摘要：

  描述了一种通过水合咪唑啉扩环合成10元和11元内酰胺的新方法。除了扩环以外，还首次发现了水合咪唑啉演化的替代过程，该过程产生了N-氨基乙基衍生物。

  DOI：

  10.1002/ejoc.202000789

文献信息

• An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene‐Fused [1.4]Oxazepines
  作者：Sergey Grintsevich、Alexander Sapegin、Elena Reutskaya、Stefan Peintner、Máté Erdélyi、Mikhail Krasavin

  DOI：10.1002/ejoc.202000789

  日期：2020.9.22

  A new approach to the synthesis of 10‐ and 11‐membered lactams via hydrated imidazoline ring expansion is described. In addition to the ring expansion an alternative course of the hydrated imidazoline evolution was discovered, for the first time, which gave N‐aminoethyl derivatives.

  描述了一种通过水合咪唑啉扩环合成10元和11元内酰胺的新方法。除了扩环以外，还首次发现了水合咪唑啉演化的替代过程，该过程产生了N-氨基乙基衍生物。
• Selective N-debenzylation of amides with p-TsOH
  作者：Ching-Yuh Chern、Yu-Ping Huang、Wai Ming Kan

  DOI：10.1016/s0040-4039(02)02738-7

  日期：2003.1

  N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxyl-benzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization. (C) 2003 Elsevier Science Ltd. All rights reserved.