(2S,3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 3-((methoxycarbonyl)amino)-2,3-diphenylpropanoate | 1609238-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 3-((methoxycarbonyl)amino)-2,3-diphenylpropanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S,3R)-3-(methoxycarbonylamino)-2,3-diphenylpropanoate
• CAS: 1609238-06-3
• 化学式: C₃₃H₃₉NO₄
• 分子量: 513.677
• InChiKey: WYRQEZGBXKOIEA-ZMTLDXPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 3-((methoxycarbonyl)amino)-2,3-diphenylpropanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以76%的产率得到(2S,3R)-3-(methylamino)-2,3-diphenylpropan-1-ol
  参考文献：
  名称：

  Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions

  摘要：

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.

  DOI：

  10.1021/jo5003505
• 作为产物：
  描述：

  三苯基硼烷 、 methyl N-phenylmethylenecarbamate 、 8-phenylmenthyl α-diazoacetate 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到(2S,3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 3-((methoxycarbonyl)amino)-2,3-diphenylpropanoate
  参考文献：
  名称：

  Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions

  摘要：

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.

  DOI：

  10.1021/jo5003505

文献信息

• Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions
  作者：Yi Luan、Jie Yu、Xiaowei Zhang、Scott E. Schaus、Ge Wang

  DOI：10.1021/jo5003505

  日期：2014.5.16

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.