(E)-3-phenyl-2-propenyl N,n-diisopropylcarbamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-phenyl-2-propenyl N,n-diisopropylcarbamate
• 英文别名: [(E)-3-phenylprop-2-enyl] N,N-di(propan-2-yl)carbamate
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: YAIZPBIHYZGVSZ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-phenyl-2-propenyl N,n-diisopropylcarbamate 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.25h， 生成 (E)-3-phenyl-1-trimethylsilyl-1-propenyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Highly Enantioenriched Homoenolate Reagents by Asymmetric γ-Deprotonation of Achiral 1-Silyl-Substituted 1-Alkenyl Carbamates

  摘要：

  1-Trimethylsilyl-1-alkenyl carbamates 1 are deprotonated by n-butyllithium/(-)-sparteine (2) with a high degree of enantiotopic differentiation in the gamma-position to form the enantiomerically enriched allyllithium derivatives 3. Trapping these with several electrophiles proceeds stereospecifically in an anti-S-E' or syn-S-E' substitution to form products 4 or ent-4, respectively. Compounds 3a (R = Me) and 3b (R = Ph) exhibit toward carbonyl electrophiles opposite senses of almost complete stereospecificity, thus for 3b(.)2 the involvement of a eta(3)-complex is suggested.

  DOI：

  10.1021/ol0364677

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.
• Preparation of Substituted Vinylsilanes from Cinnamyl Carbamates
  作者：Paul H. Mason、Neville D. Emslie

  DOI：10.1080/00397919608003513

  日期：1996.4

  Reaction of N,N-diethyl cinnamyl carbamate with TBDMSCl yields the mono-silylated carbamate which, on treatment with butyllithium, reacts with various electrophiles to give the corresponding disubstituted carbamates.
• Highly Enantioenriched Homoenolate Reagents by Asymmetric γ-Deprotonation of Achiral 1-Silyl-Substituted 1-Alkenyl Carbamates
  作者：Jenny Reuber、Roland Fröhlich、Dieter Hoppe

  DOI：10.1021/ol0364677

  日期：2004.3.1

  1-Trimethylsilyl-1-alkenyl carbamates 1 are deprotonated by n-butyllithium/(-)-sparteine (2) with a high degree of enantiotopic differentiation in the gamma-position to form the enantiomerically enriched allyllithium derivatives 3. Trapping these with several electrophiles proceeds stereospecifically in an anti-S-E' or syn-S-E' substitution to form products 4 or ent-4, respectively. Compounds 3a (R = Me) and 3b (R = Ph) exhibit toward carbonyl electrophiles opposite senses of almost complete stereospecificity, thus for 3b(.)2 the involvement of a eta(3)-complex is suggested.