(R)-1-(4-methoxyphenyl)-2-phenyl-2-((trimethylsilyl)oxy)propan-1-one | 1225468-90-5

• 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: (R)-1-(4-methoxyphenyl)-2-phenyl-2-((trimethylsilyl)oxy)propan-1-one
• 英文别名: (2R)-1-(4-methoxyphenyl)-2-phenyl-2-trimethylsilyloxypropan-1-one
• CAS: 1225468-90-5
• 化学式: C₁₉H₂₄O₃Si
• 分子量: 328.483
• InChiKey: FXZBYMMMXHMTRR-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-phenyl-2-(trimethylsilyloxy)propan-1-one 在 硼烷四氢呋喃络合物 、 (R)-2-methoxy-CBS-oxazaborolidine 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 甲醇 、 水 为溶剂， 反应 7.0h， 生成 (R)-1-(4-methoxyphenyl)-2-phenyl-2-((trimethylsilyl)oxy)propan-1-one 、 (S)-1-(4-methoxyphenyl)-2-phenyl-2-((trimethylsilyl)oxy)propan-1-one 、 (1R,2S)-1-(4-methoxyphenyl)-2-phenyl-2-trimethylsilyloxypropan-1-ol
  参考文献：
  名称：

  Lanthanum Tricyanide-Catalyzed Acyl Silane−Ketone Benzoin Additions and Kinetic Resolution of Resultant α-Silyloxyketones

  摘要：

  We report the full account of our efforts on the lanthanum tricyanide-catalyzed acyl silane ketone benzoin reaction. The reaction exhibits a wide scope in both acyl silane (aryl, alkyl) and ketone (arylalkyl, alkyl-alkyl, aryl-aryl, alkenyl-alkyl, alkynyl-alkyl) coupling partners. The diastereoselectivity of the reaction has been examined in both cyclic and acyclic systems. Cyclohexanones give products arising from equatorial attack by the acyl silane. The diastereoselectivity of acyl silane addition to acyclic alpha-hydroxy ketones can be controlled by varying the protecting group to obtain either Felkin-Ahn or chelation control. The resultant alpha-silyloxyketone products can be resolved with selectivity factors from 10 to 15 by subjecting racemic ketone benzoin products to CBS reduction.

  DOI：

  10.1021/jo100312w

文献信息

• Lanthanum Tricyanide-Catalyzed Acyl Silane−Ketone Benzoin Additions and Kinetic Resolution of Resultant α-Silyloxyketones
  作者：James C. Tarr、Jeffrey S. Johnson

  DOI：10.1021/jo100312w

  日期：2010.5.21

  We report the full account of our efforts on the lanthanum tricyanide-catalyzed acyl silane ketone benzoin reaction. The reaction exhibits a wide scope in both acyl silane (aryl, alkyl) and ketone (arylalkyl, alkyl-alkyl, aryl-aryl, alkenyl-alkyl, alkynyl-alkyl) coupling partners. The diastereoselectivity of the reaction has been examined in both cyclic and acyclic systems. Cyclohexanones give products arising from equatorial attack by the acyl silane. The diastereoselectivity of acyl silane addition to acyclic alpha-hydroxy ketones can be controlled by varying the protecting group to obtain either Felkin-Ahn or chelation control. The resultant alpha-silyloxyketone products can be resolved with selectivity factors from 10 to 15 by subjecting racemic ketone benzoin products to CBS reduction.