Trimethyl-(2-phenylsulfanyl-propoxy)-silane | 141510-50-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Trimethyl-(2-phenylsulfanyl-propoxy)-silane
• 英文别名: Trimethyl(2-phenylsulfanylpropoxy)silane；trimethyl(2-phenylsulfanylpropoxy)silane
• CAS: 141510-50-1
• 化学式: C₁₂H₂₀OSSi
• 分子量: 240.442
• InChiKey: SFCBAEBIMSALDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯硫酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 咪唑 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 Trimethyl-(2-phenylsulfanyl-propoxy)-silane
  参考文献：
  名称：

  Highly regioselective and stereospecific functionalization of 1,2-propanediol with trimethyl(X)silanes employing the 1,3,2.lambda.5-dioxaphospholane methodology

  摘要：

  The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2-lambda-5-dioxaphospholane (2) [prepared from the bis(transoxyphosphoranylation) of (S)-1,2-propanediol (1) with diethoxytriphenylphosphorane (DTPP)] was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br, Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts. A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominantly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).

  DOI：

  10.1021/jo00038a032

文献信息

• Highly regioselective and stereospecific functionalization of 1,2-propanediol with trimethyl(X)silanes employing the 1,3,2.lambda.5-dioxaphospholane methodology
  作者：Isabel Mathieu-Pelta、Slayton A. Evans

  DOI：10.1021/jo00038a032

  日期：1992.6

  The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2-lambda-5-dioxaphospholane (2) [prepared from the bis(transoxyphosphoranylation) of (S)-1,2-propanediol (1) with diethoxytriphenylphosphorane (DTPP)] was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br, Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts. A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominantly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).