(M,R)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene | 794469-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (M,R)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene
• 英文别名: (P,S)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene；(P,R)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene；(M,S)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene；N-[[1-(2-methoxy-4,6-dimethylphenyl)naphthalen-2-yl]methyl]-N-methyl-1-phenylethanamine
• CAS: 794469-18-4；794469-19-5；794469-21-9；727705-69-3
• 化学式: C₂₉H₃₁NO
• 分子量: 409.571
• InChiKey: BURFVPOAEZBBGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (M,R)-1-(2-methoxy-4,6-dimethylphenyl)-2-[N-methyl-N-(1-phenylethyl)aminomethyl]naphthalene 、 三氟甲磺酸酐 在 氢溴酸 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以76%的产率得到(M,R)-1-(2-trifluoromethanesulfonyloxy-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-N-甲基-苯乙胺 、 (M)-2-bromomethyl-1-(2-methoxy-4,6-dimethylphenyl)naphthalene 以 二氯甲烷 为溶剂， 以84%的产率得到(M,R)-1-(2-methoxy-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