(E)-3-(1-naphthyl)-prop-2-enyl N,N-diisiopropylcarbamate | 1242027-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-3-(1-naphthyl)-prop-2-enyl N,N-diisiopropylcarbamate
• CAS: 1242027-12-8
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: QFKYDGGVJMVVOD-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (E)-3-(1-naphthyl)-prop-2-enyl N,N-diisiopropylcarbamate 在 (2-methylpropyl)lithium 、 (S,S)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.08h， 以80%的产率得到(1S)-(E)-3-(1-naphthyl)-1-trimethylsilyl-prop-2-enyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Configurationally Labile Enantioenriched Lithiated 3-Arylprop-2-enyl Carbamates: Joint Experimental and Quantum Chemical Investigations on the Equilibrium of Epimers

  摘要：

  Experimental investigations as well as high-level quantum chemical calculations are performed on the two epimeric pairs of complexes 4.2 and 6.2 obtained by lithiation of cinnamyl carbamate (1) and 1-naphthyl derivative 5 in the presence of BOX ligands (S,S)- and (R,R)-2. Indeed, in the case of configurationally labile complexes and a dynamic thermodynamic resolution, which is found to take place, one of both epimers is energetically favored. The quantum chemical computations allow the prediction of the enantiomeric excess that can be expected.

  DOI：

  10.1021/jo101218z
• 作为产物：
  描述：

  二异丙基甲胺酰氯 、 (E)-3-(1-naphthyl)prop-2-en-1-ol 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.25h， 以75%的产率得到(E)-3-(1-naphthyl)-prop-2-enyl N,N-diisiopropylcarbamate
  参考文献：
  名称：

  Configurationally Labile Enantioenriched Lithiated 3-Arylprop-2-enyl Carbamates: Joint Experimental and Quantum Chemical Investigations on the Equilibrium of Epimers

  摘要：

  Experimental investigations as well as high-level quantum chemical calculations are performed on the two epimeric pairs of complexes 4.2 and 6.2 obtained by lithiation of cinnamyl carbamate (1) and 1-naphthyl derivative 5 in the presence of BOX ligands (S,S)- and (R,R)-2. Indeed, in the case of configurationally labile complexes and a dynamic thermodynamic resolution, which is found to take place, one of both epimers is energetically favored. The quantum chemical computations allow the prediction of the enantiomeric excess that can be expected.

  DOI：

  10.1021/jo101218z