5-Oxo-5-phenyl-pentanoic acid 2,4-dimethoxy-benzylamide | 583027-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Oxo-5-phenyl-pentanoic acid 2,4-dimethoxy-benzylamide
• 英文别名: N-[(2,4-dimethoxyphenyl)methyl]-5-oxo-5-phenylpentanamide
• CAS: 583027-32-1
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: UNLOXVHUBNIZSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Oxo-5-phenyl-pentanoic acid 2,4-dimethoxy-benzylamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以92%的产率得到6-Phenyl-1,2,3,4-tetrahydropyridin-2-on
  参考文献：
  名称：

  One‐Pot Synthesis of Ene‐Lactams viaN‐Debenzylation of Keto‐ContainingN‐2,4‐Dimethoxylbenzylamides

  摘要：

  A general method of ene-lactam preparation is described. Ene-lactams can be prepared efficiently from keto-containing N-2,4-dimethoxylbenzylamides in good to excellent yields. This method is applicable for the preparation of substituted delta-, gamma-. and epsilon-ene-lactams and bicyclic ene-lactams.

  DOI：

  10.1081/scc-200039335
• 作为产物：
  描述：

  5-Hydroxy-5-phenyl-pentanoic acid 2,4-dimethoxy-benzylamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以34%的产率得到5-Oxo-5-phenyl-pentanoic acid 2,4-dimethoxy-benzylamide
  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

文献信息

• One‐Pot Synthesis of Ene‐Lactams via<i>N</i>‐Debenzylation of Keto‐Containing<i>N</i>‐2,4‐Dimethoxylbenzylamides
  作者：Wai Ming Kan、Ching‐Lung Cheng、Ching‐Yuh Chern

  DOI：10.1081/scc-200039335

  日期：2004.12.31

  A general method of ene-lactam preparation is described. Ene-lactams can be prepared efficiently from keto-containing N-2,4-dimethoxylbenzylamides in good to excellent yields. This method is applicable for the preparation of substituted delta-, gamma-. and epsilon-ene-lactams and bicyclic ene-lactams.
• 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.