(M,S)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[N-(1-phenylethyl)aminomethyl]naphthalene | 253430-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (M,S)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[N-(1-phenylethyl)aminomethyl]naphthalene
• 英文别名: (M,R)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[N-(1-phenylethyl)aminomethyl]naphthalene；3,5-dimethyl-2-[2-[(1-phenylethylamino)methyl]naphthalen-1-yl]phenol
• CAS: 253430-33-0
• 化学式: C₂₇H₂₇NO
• 分子量: 381.517
• InChiKey: RRBGSWBLTVAGBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (M,S)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[N-(1-phenylethyl)aminomethyl]naphthalene 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以41%的产率得到(M,R)-1-(2-acetoxy-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：

  (M,S)-1-(2-benzyloxy-4,6-dimethylphenyl)-2-[N-(1-phenylethyl)aminomethyl]naphthalene 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 以95%的产率得到(M,S)-1-(2-hydroxy-4,6-dimethylphenyl)-2-[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