1-(2-hydroxy-4,6-dimethylphenyl)-N-(1-phenylethyl)naphthalene-2-carboxamide | 253432-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxy-4,6-dimethylphenyl)-N-(1-phenylethyl)naphthalene-2-carboxamide
• CAS: 253432-11-0
• 化学式: C₂₇H₂₅NO₂
• 分子量: 395.501
• InChiKey: PTRJINOIXTWIIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4,6-dimethylphenyl)-N-(1-phenylethyl)naphthalene-2-carboxamide 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢溴酸 、 四丁基碘化铵 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 123.0h， 生成 (M,R)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene
  参考文献：
  名称：

  Synthesis and antitrypanosomal activity of 2-aminomethyl-1-(2-oxyphenyl)naphthalenes

  摘要：

  A broad variety of enantiopure, axially chiral 2-aminomethyl-1-(2-oxyphenyl)naphthalenes were prepared via short and efficient synthetic pathways by using the 'lactone method' for the regio- and stereoselective construction of the biaryl axis. Their in vitro activity against Trypanosoma cruzi the causative agent of Chagas' disease, was evaluated. In particular, the M-configured atropisomers, with the 2-oxy function equipped with an O-triflate group, were found to exhibit good antitrypanosomal activities (down to IC50=1.6 mug/mL), combined with low levels of cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.076
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 (±)-1,3-dimethyl-6H-benzo[b]naphtho[1,2-d]pyranone 在 sodium hydride 作用下， 以84%的产率得到1-(2-hydroxy-4,6-dimethylphenyl)-N-(1-phenylethyl)naphthalene-2-carboxamide
  参考文献：
  名称：

  Synthesis and antitrypanosomal activity of 2-aminomethyl-1-(2-oxyphenyl)naphthalenes

  摘要：

  A broad variety of enantiopure, axially chiral 2-aminomethyl-1-(2-oxyphenyl)naphthalenes were prepared via short and efficient synthetic pathways by using the 'lactone method' for the regio- and stereoselective construction of the biaryl axis. Their in vitro activity against Trypanosoma cruzi the causative agent of Chagas' disease, was evaluated. In particular, the M-configured atropisomers, with the 2-oxy function equipped with an O-triflate group, were found to exhibit good antitrypanosomal activities (down to IC50=1.6 mug/mL), combined with low levels of cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.076

文献信息

• Synthesis and antitrypanosomal activity of 2-aminomethyl-1-(2-oxyphenyl)naphthalenes
  作者：Gerhard Bringmann、Robert-Michael Pfeifer、Petra Schreiber、Kristina Hartner、Nikolaus Kocher、Reto Brun、Karl Peters、Eva-Maria Peters、Matthias Breuning

  DOI：10.1016/j.tet.2004.05.076

  日期：2004.7

  A broad variety of enantiopure, axially chiral 2-aminomethyl-1-(2-oxyphenyl)naphthalenes were prepared via short and efficient synthetic pathways by using the 'lactone method' for the regio- and stereoselective construction of the biaryl axis. Their in vitro activity against Trypanosoma cruzi the causative agent of Chagas' disease, was evaluated. In particular, the M-configured atropisomers, with the 2-oxy function equipped with an O-triflate group, were found to exhibit good antitrypanosomal activities (down to IC50=1.6 mug/mL), combined with low levels of cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.