(E)-2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1-phenyl-but-2-en-1-one | 192751-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1-phenyl-but-2-en-1-one
• 英文别名: (E)-2-[tert-butyl-methyl-(phenylmethoxymethyl)silyl]-1-phenylbut-2-en-1-one
• CAS: 192751-88-5
• 化学式: C₂₃H₃₀O₂Si
• 分子量: 366.576
• InChiKey: GFISJOYITBUTAS-AERZKKPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1-phenyl-but-2-en-1-one 在 四甲基乙二胺 、 硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 1,3-联苯-1-丁酮
  参考文献：
  名称：

  A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to α,β-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone

  摘要：

  The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with alpha-silylated alpha,beta-unsaturated ketones afforded the respective addition products with pi-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00134-1
• 作为产物：
  描述：

  (E)-2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1-phenyl-but-2-en-1-ol 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 以98%的产率得到(E)-2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1-phenyl-but-2-en-1-one
  参考文献：
  名称：

  A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to α,β-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone

  摘要：

  The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with alpha-silylated alpha,beta-unsaturated ketones afforded the respective addition products with pi-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00134-1

文献信息

• A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to α,β-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone
  作者：Svestoslav Bratovanov、Stefan Bienz

  DOI：10.1016/s0957-4166(97)00134-1

  日期：1997.5

  The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with alpha-silylated alpha,beta-unsaturated ketones afforded the respective addition products with pi-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group. (C) 1997 Elsevier Science Ltd.