(R)-4-methyl-1-phenyl-3-(phenyldimethylsilyl)-1-pentanone | 115826-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-methyl-1-phenyl-3-(phenyldimethylsilyl)-1-pentanone
• 英文别名: (3R)-3-[dimethyl(phenyl)silyl]-4-methyl-1-phenylpentan-1-one
• CAS: 115826-98-7
• 化学式: C₂₀H₂₆OSi
• 分子量: 310.511
• InChiKey: JFCWXXPREIJLNC-HXUWFJFHSA-N

物化性质

• 沸点：
  413.0±28.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-4-methyl-1-phenyl-3-(phenyldimethylsilyl)-1-pentanone 在 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 potassium hydrogencarbonate 、 双氧水 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲醇 为溶剂， 反应 10.25h， 以89%的产率得到(R)-3-hydroxy-4-methyl-1-phenylpentan-1-one
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Allylsilanes through Rhodium/Chiral Diene-Catalyzed 1,4-Addition of Alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes

  摘要：

  A new synthetic method of chiral allylsilanes has been developed through a rhodium-catalyzed asymmetric 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes to beta-silyl alpha,beta-unsaturated ketones. By employing (S,S)-Ph-bod* as a ligand, a range of alkenyl nucleophiles have been installed to these substrates in high yield and enantiomeric excess. The resulting allylsilanes can be used for stereoselective intramolecular allylation reactions to control two contiguous tertiary and quaternary stereocenters.

  DOI：

  10.1021/ol702125q
• 作为产物：
  描述：

  C₂₀H₂₄OSi 在 RhCl(PPh₃)3 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以92%的产率得到(R)-4-methyl-1-phenyl-3-(phenyldimethylsilyl)-1-pentanone
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Allylsilanes through Rhodium/Chiral Diene-Catalyzed 1,4-Addition of Alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes

  摘要：

  A new synthetic method of chiral allylsilanes has been developed through a rhodium-catalyzed asymmetric 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes to beta-silyl alpha,beta-unsaturated ketones. By employing (S,S)-Ph-bod* as a ligand, a range of alkenyl nucleophiles have been installed to these substrates in high yield and enantiomeric excess. The resulting allylsilanes can be used for stereoselective intramolecular allylation reactions to control two contiguous tertiary and quaternary stereocenters.

  DOI：

  10.1021/ol702125q

文献信息

• Catalytic asymmetric synthesis of β-hydroxy ketones by palladium-catalyzed asymmetric 1,4-disilylation of α,β-unsaturated ketones
  作者：Yonetatsu Matsumoto、Tamio Hayashi、Yoshihiko Ito

  DOI：10.1016/s0040-4020(01)80758-4

  日期：1994.1

  1,4-Disilylation of β,β-unsaturated ketones with 1,1-dichloro-l-phenyl-2,2,2-trimethyldisilane proceeded in the presence of phosphine-palladium catalysts in benzene. High enantio-selectivity (up to 92%) was observed in the disilylation with dichloro[(R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) as a catalyst (0.5 mol %). The disilylation products, 1-(trimethyisilyloxy)-3-(dichlorophenylsilyl)propenes

  在苯存在膦-钯催化剂的情况下，将β，β-不饱和酮与1,1-二氯-1-苯基-2,2,2-三甲基乙硅烷进行1,4-二甲化。使用二氯[（R）-2,2'-双（二苯基膦基）-1,1'-联萘]钯（II）（0.5 mol％ ）。容易将二甲硅烷基化产物1-（三甲基甲硅烷基氧基）-3-（二氯苯基甲硅烷基）丙烯转化为旋光性的α-未取代或抗α-取代的β-（苯基二甲基甲硅烷基）酮，其氧化反应生成相应的旋光性β-羟基酮高产。
• Palladium-catalyzed asymmetric 1,4-disilylation of .alpha.,.beta.-unsaturated ketones: catalytic asymmetric synthesis of .beta.-hydroxy ketones
  作者：Tamio. Hayashi、Yonetatsu. Matsumoto、Yoshihiko. Ito

  DOI：10.1021/ja00224a057

  日期：1988.8