1-(4-methylnaphthalen-1-yl)-prop-2-en-1-amine | 1270575-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-methylnaphthalen-1-yl)-prop-2-en-1-amine
• 英文别名: 1-(4-Methylnaphthalen-1-yl)prop-2-en-1-amine
• CAS: 1270575-12-6
• 化学式: C₁₄H₁₅N
• mdl: MFCD18659923
• 分子量: 197.28
• InChiKey: WXCGBDVCYMPADJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲氧基乙酸乙酯 、 1-(4-methylnaphthalen-1-yl)-prop-2-en-1-amine 在 immobilized lipase B from Candida antarctica 作用下， 以 甲基叔丁基醚 为溶剂， 反应 48.0h， 以48%的产率得到(S)-1-(4-methylnaphthalen-1-yl)prop-2-en-1-amine
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004
• 作为产物：
  描述：

  (E)-3-(4-methylnaphthalen-1-yl)-allyl-2,2,2-trichloroacetimidate 在 potassium carbonate 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 1-(4-methylnaphthalen-1-yl)-prop-2-en-1-amine
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004