(1R)-N-benzyloxycarbonyl-1-isopropyl-4-pentenamine | 943231-56-9

• 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: (1R)-N-benzyloxycarbonyl-1-isopropyl-4-pentenamine
• 英文别名: benzyl N-[(3R)-2-methylhept-6-en-3-yl]carbamate
• CAS: 943231-56-9
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: WKTVTBIHOFPENJ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (1R)-N-benzyloxycarbonyl-1-isopropyl-4-pentenamine 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (2R,5R)-N-benzyloxycarbonyl-5-(2-oxopropyl)-2-isopropylpyrrolidine 、 (2R,5S)-N-benzyloxycarbonyl-5-(2-oxopropyl)-2-isopropylpyrrolidine
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829
• 作为产物：
  描述：

  4-戊烯醛 在 盐酸 、 titanium(IV) tetraethanolate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.33h， 生成 (1R)-N-benzyloxycarbonyl-1-isopropyl-4-pentenamine
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829

文献信息

• Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives
  作者：Santos Fustero、Diego Jiménez、María Sánchez-Roselló、Carlos del Pozo

  DOI：10.1021/ja0709829

  日期：2007.5.1

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.