(1S)-(E)-3-(1-naphthyl)-1-trimethylsilyl-prop-2-enyl N,N-diisopropylcarbamate | 1242027-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S)-(E)-3-(1-naphthyl)-1-trimethylsilyl-prop-2-enyl N,N-diisopropylcarbamate
• 英文别名: [(E,1S)-3-naphthalen-1-yl-1-trimethylsilylprop-2-enyl] N,N-di(propan-2-yl)carbamate
• CAS: 1242027-11-7
• 化学式: C₂₃H₃₃NO₂Si
• 分子量: 383.606
• InChiKey: VZGZDFBBYNRDNP-BQXQKYNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• Configurationally Labile Enantioenriched Lithiated 3-Arylprop-2-enyl Carbamates: Joint Experimental and Quantum Chemical Investigations on the Equilibrium of Epimers
  作者：Thérèse Hémery、Robert Huenerbein、Roland Fröhlich、Stefan Grimme、Dieter Hoppe

  DOI：10.1021/jo101218z

  日期：2010.8.20

  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.