(R)-3-(methoxyamino)-5-methyl-1-phenyl-1-hexanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(methoxyamino)-5-methyl-1-phenyl-1-hexanone
• 英文别名: (S)-3-(methoxyamino)-5-methyl-1-phenylhexan-1-one；(3S)-3-(methoxyamino)-5-methyl-1-phenylhexan-1-one
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: UGSXYLUKWDNEAO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯甲酰乙腈 、 5-甲基-1-苯基己-2-烯-1-酮 在 (S)-YLi₃[tris(binaphthoxide)] 、 calcium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (S)-3-(methoxyamino)-5-methyl-1-phenyl-1-hexanone 、 (R)-3-(methoxyamino)-5-methyl-1-phenyl-1-hexanone
  参考文献：
  名称：

  Heterobimetallic Catalysis in Asymmetric 1,4-Addition of O-Alkylhydroxylamine to Enones

  摘要：

  A heterobimetallic YLi3tris(binaphthoxide) catalyst (YLB) promoted a 1,4-addition of O-methylhydroxylamine in high enantiomeric excess (up to 97% ee). Catalyst loading was reduced to as little as 0.5 mol %, still affording the 1,4-adduct in 96% yield and 96% ee. A high concentration of substrates and the scalability of the present system is also practically useful. The results suggested that the heterobimetallic catalysis was not deactivated even in the presence of excess amine under highly concentrated conditions. A Y and Li bimetallic cooperative function was essential for a high catalyst turnover number.

  DOI：

  10.1021/ja038688d

文献信息

• Heterobimetallic Catalysis in Asymmetric 1,4-Addition of <i>O</i>-Alkylhydroxylamine to Enones
  作者：Noriyuki Yamagiwa、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja038688d

  日期：2003.12.1

  A heterobimetallic YLi3tris(binaphthoxide) catalyst (YLB) promoted a 1,4-addition of O-methylhydroxylamine in high enantiomeric excess (up to 97% ee). Catalyst loading was reduced to as little as 0.5 mol %, still affording the 1,4-adduct in 96% yield and 96% ee. A high concentration of substrates and the scalability of the present system is also practically useful. The results suggested that the heterobimetallic catalysis was not deactivated even in the presence of excess amine under highly concentrated conditions. A Y and Li bimetallic cooperative function was essential for a high catalyst turnover number.