Triphenyl-[phenyl(phenylsulfanyl)methyl]silane | 159956-87-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Triphenyl-[phenyl(phenylsulfanyl)methyl]silane
• CAS: 159956-87-3
• 化学式: C₃₁H₂₆SSi
• 分子量: 458.699
• InChiKey: MIWCTADDCJFCTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Triphenyl-[phenyl(phenylsulfanyl)methyl]silane 在 萘 、 六氯丙酮 、 lithium 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 (顺式)-1,1'-(1,2-环丙烷二基)二苯
  参考文献：
  名称：

  通过手性环氧化物与外消旋α-甲硅烷基有机锂试剂反应，对映选择性合成γ-羟基硅烷，1,3-二醇和环丙烷

  摘要：

  外消旋α-甲硅烷基有机锂试剂2a和2b与（R）-氧化苯乙烯对映选择性地反应，分别生成手性γ-羟基硅烷3a和3b。从这些γ-羟基硅烷容易以对映体纯的形式获得手性1，3-二醇4和环丙烷7。

  DOI：

  10.1016/s0040-4039(00)78483-8
• 作为产物：
  描述：

  硫代苯甲酰三苯基硅烷 、 苯基溴化镁 以 乙醚 为溶剂， 生成 Triphenyl-[phenyl(phenylsulfanyl)methyl]silane
  参考文献：
  名称：

  Reactions between Grignard Reagents and Thiocarbonyl Compounds:  A Revisitation

  摘要：

  The radical anions from thiobenzophenone, thiobenzoyltriphenylsilane, and 3,5-di-tert-butylthiobenzoyltriphenylsilane were detected by EPR spectroscopy when these compounds were reacted with a number of Grignard reagents, RMgBr. The radical adducts resulting from addition of R-. radicals to the thiones were also detected. The formation of the radical anions indicates unambiguously the occurrence of a SET process which might be the initial stage of these reactions. In the case of tris(trimethylsilyl)ethanethial only the radical adducts were detected. The first reduction potentials of these thiones have also been measured in order to verify the feasibility of the SET process. In agreement with the EPR experiments, the calculated standard free energy changes suggest that electron transfer is possible in the first three cases and disfavored with the thioaldehyde.

  DOI：

  10.1021/jo9708001

文献信息

• Reactions between Grignard Reagents and Thiocarbonyl Compounds:  A Revisitation
  作者：Angelo Alberti、Massimo Benaglia、Dante Macciantelli、Massimo Marcaccio、Antonio Olmeda、Gian Franco Pedulli、Sergio Roffia

  DOI：10.1021/jo9708001

  日期：1997.9.1

  The radical anions from thiobenzophenone, thiobenzoyltriphenylsilane, and 3,5-di-tert-butylthiobenzoyltriphenylsilane were detected by EPR spectroscopy when these compounds were reacted with a number of Grignard reagents, RMgBr. The radical adducts resulting from addition of R-. radicals to the thiones were also detected. The formation of the radical anions indicates unambiguously the occurrence of a SET process which might be the initial stage of these reactions. In the case of tris(trimethylsilyl)ethanethial only the radical adducts were detected. The first reduction potentials of these thiones have also been measured in order to verify the feasibility of the SET process. In agreement with the EPR experiments, the calculated standard free energy changes suggest that electron transfer is possible in the first three cases and disfavored with the thioaldehyde.
• Enantioselective synthesis of γ-hydroxysilanes, 1,3-diols and cyclopropanes by reaction of a chiral epoxide with a racemic α-silyl organolithium reagent
  作者：E.J. Corey、Zhuoliang Chen

  DOI：10.1016/s0040-4039(00)78483-8

  日期：1994.11

  The racemic α-silyl organolithium reagents 2a and 2b react with (R)-styrene oxide enantioselectively to produce the chiral γ-hydroxysilanes 3a and 3b, respectively. The chiral 1,3-diol 4 and cyclopropane 7 are readily obtained in enantiomerically pure form from these γ-hydroxysilanes.

  外消旋α-甲硅烷基有机锂试剂2a和2b与（R）-氧化苯乙烯对映选择性地反应，分别生成手性γ-羟基硅烷3a和3b。从这些γ-羟基硅烷容易以对映体纯的形式获得手性1，3-二醇4和环丙烷7。