(E)-cinnamyl (2-chloromethylphenyl)carbamate | 1403743-37-2

• 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)-cinnamyl (2-chloromethylphenyl)carbamate
• 英文别名: [(E)-3-phenylprop-2-enyl] N-[2-(chloromethyl)phenyl]carbamate
• CAS: 1403743-37-2
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: UHFOZXIAVHYPCN-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-cinnamyl (2-chloromethylphenyl)carbamate 在 potassium phosphate 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以56%的产率得到4-phenyl-3,3a,4,5-tetrahydrooxazolo[3,4-a]quinolin-1-one
  参考文献：
  名称：

  Application of a Cross-Metathesis and Intramolecular Aza-Diels-Alder Sequence to the Synthesis of trans-2,3-Disubstituted Tetrahydroquinolines

  摘要：

  The synthesis of 2,3-disubstituted tetrahydroquinolines has been achieved by first performing a cross-metathesis of different alkenes with readily available N-allyloxycarbonyl-2-chloro-methylaniline. Among the catalysts tested, Hoveyda-Grubbs reagent appeared to be the most suitable, reaching the substituted analogues with complete E-stereocontrol and convenient yields. An intramolecular aza-Diels-Alder reaction was further carried out in the presence of potassium phosphate as promoter to deliver the corresponding 2,3-disubstituted tetrahydroquinolines.

  DOI：

  10.1055/s-0031-1289790
• 作为产物：
  描述：

  苯乙烯 、 (2-氯甲基苯基)氨基甲酸烯丙酯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到(E)-cinnamyl (2-chloromethylphenyl)carbamate
  参考文献：
  名称：

  Application of a Cross-Metathesis and Intramolecular Aza-Diels-Alder Sequence to the Synthesis of trans-2,3-Disubstituted Tetrahydroquinolines

  摘要：

  The synthesis of 2,3-disubstituted tetrahydroquinolines has been achieved by first performing a cross-metathesis of different alkenes with readily available N-allyloxycarbonyl-2-chloro-methylaniline. Among the catalysts tested, Hoveyda-Grubbs reagent appeared to be the most suitable, reaching the substituted analogues with complete E-stereocontrol and convenient yields. An intramolecular aza-Diels-Alder reaction was further carried out in the presence of potassium phosphate as promoter to deliver the corresponding 2,3-disubstituted tetrahydroquinolines.

  DOI：

  10.1055/s-0031-1289790

文献信息

• Application of a Cross-Metathesis and Intramolecular Aza-Diels-Alder Sequence to the Synthesis of trans-2,3-Disubstituted Tetrahydroquinolines
  作者：Olivier Piva、Sophie Feuillastre、Vincent Pellet

  DOI：10.1055/s-0031-1289790

  日期：2012.8

  The synthesis of 2,3-disubstituted tetrahydroquinolines has been achieved by first performing a cross-metathesis of different alkenes with readily available N-allyloxycarbonyl-2-chloro-methylaniline. Among the catalysts tested, Hoveyda-Grubbs reagent appeared to be the most suitable, reaching the substituted analogues with complete E-stereocontrol and convenient yields. An intramolecular aza-Diels-Alder reaction was further carried out in the presence of potassium phosphate as promoter to deliver the corresponding 2,3-disubstituted tetrahydroquinolines.