1,1-bis{[(dimethyl)phenylsilyl]methyl}-4-phenyl-1-pentene | 683773-82-2

• 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: 1,1-bis{[(dimethyl)phenylsilyl]methyl}-4-phenyl-1-pentene
• 英文别名: 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene；[2-[[Dimethyl(phenyl)silyl]methyl]-5-phenylpent-2-enyl]-dimethyl-phenylsilane
• CAS: 683773-82-2
• 化学式: C₂₈H₃₆Si₂
• 分子量: 428.765
• InChiKey: DXLXZKDAWSWBGP-UHFFFAOYSA-N

物化性质

• 沸点：
  524.8±50.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-bis{[(dimethyl)phenylsilyl]methyl}-4-phenyl-1-pentene 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到2-[(Dimethyl-phenyl-silanyl)-methyl]-5-phenyl-pent-1-en-3-ol
  参考文献：
  名称：

  Reactions of 1,1-Bis(silylmethyl)-1-alkene with N-Halosuccinimide and Ozone

  摘要：

  Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-l-pentene (5) and 3-halo-5-phenyl-1,2bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).

  DOI：

  10.3987/com-05-s(k)37
• 作为产物：
  描述：

  magnesium,methanidyl-dimethyl-phenylsilane,chloride 、 4-phenyl-1,1-dibromo-1-butene 在 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以73%的产率得到1,1-bis{[(dimethyl)phenylsilyl]methyl}-4-phenyl-1-pentene
  参考文献：
  名称：

  Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

  摘要：

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).

  DOI：

  10.3987/com-03-s52

文献信息

• Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone
  作者：Jun'ichi Uenishi、Masashi Ohmi

  DOI：10.3987/com-03-s52

  日期：——

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).
• Reactions of 1,1-Bis(silylmethyl)-1-alkene with N-Halosuccinimide and Ozone
  作者：Jun'ichi Uenishi、Yusuke Tanaka、Masashi Ohmi、Hotsumi Shimomura、Nobuyuki Kawai

  DOI：10.3987/com-05-s(k)37

  日期：——

  Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-l-pentene (5) and 3-halo-5-phenyl-1,2bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).