(1S,2R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone | 950585-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,2R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone
• 英文别名: [(1S,2R)-2-(2-methoxyphenyl)cyclohexyl]-dimethyl-phenylsilane
• CAS: 950585-03-2
• 化学式: C₂₁H₂₈OSi
• 分子量: 324.538
• InChiKey: BZLBEDSFXFEPND-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone 在 bis(trifluoromethanesulfonyl)imide 作用下， 以 二氯甲烷 为溶剂， 生成 (6aS,10aR)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c][1,2]benzoxasiline
  参考文献：
  名称：

  The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts

  摘要：

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.086
• 作为产物：
  描述：

  2-(2-methoxyphenyl)cyclohex-2-enone 在 chiral AD column 、 lithium 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 异丙醇 为溶剂， 反应 5.5h， 生成 (1S,2R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone
  参考文献：
  名称：

  The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts

  摘要：

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.086

文献信息

• The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts
  作者：Zilong Tang、Benoit Mathieu、Bernard Tinant、Georges Dive、Léon Ghosez

  DOI：10.1016/j.tet.2007.05.086

  日期：2007.8

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.