(S,E)-dimethyl(phenyl)(1-phenylhex-4-en-3-yl)silane | 1270304-79-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S,E)-dimethyl(phenyl)(1-phenylhex-4-en-3-yl)silane
• 英文别名: dimethylphenyl((3S,4E)-1-phenyl-4-hexen-3-yl)silane；dimethyl-phenyl-[(E,3S)-1-phenylhex-4-en-3-yl]silane
• CAS: 1270304-79-4
• 化学式: C₂₀H₂₆Si
• 分子量: 294.512
• InChiKey: BRXOAJLLTFFJIK-OINDORCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-phenylpropyl N,N-diisopropylcarbamate 在 叔丁基锂 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 环己烷 、 正戊烷 为溶剂， 反应 6.0h， 生成 (S,E)-dimethyl(phenyl)(1-phenylhex-4-en-3-yl)silane
  参考文献：
  名称：

  Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates

  摘要：

  Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.

  DOI：

  10.1021/ol200177f

文献信息

• Reversible 1,3-<i>anti</i>/<i>syn</i>-Stereochemical Courses in Copper-Catalyzed γ-Selective Allyl–Alkyl Coupling between Chiral Allylic Phosphates and Alkylboranes
  作者：Kazunori Nagao、Umi Yokobori、Yusuke Makida、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ja302520h

  日期：2012.5.30

  The stereochemical courses of the copper-catalyzed allyl-alkyl coupling between enantioenriched chiral allylic phosphates and alkylboranes were switchable between 1,3-anti and 1,3-syn selectivities by the choice of solvents and achiral alkoxide bases with different steric demands. The reactions with gamma-silylated allylic phosphates allow efficient synthesis of enantioenriched chiral allylsilanes with tertiary or quaternary carbon stereogenic centers. Cyclic and acyclic bimodal participation of alkoxyborane species in an organocopper addition-elimination sequence is proposed to account for the phenomenon of the anti/syn-stereochemical reversal.
• Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates
  作者：Varinder K. Aggarwal、Michael Binanzer、M. Carolina de Ceglie、Maddalena Gallanti、Ben W. Glasspoole、Stephanie J. F. Kendrick、Ravindra P. Sonawane、Ana Vázquez-Romero、Matthew P. Webster

  DOI：10.1021/ol200177f

  日期：2011.3.18

  Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.