tris(trimethylsilyl)methyl methyl sulfide | 31704-09-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: tris(trimethylsilyl)methyl methyl sulfide
• 英文别名: tris(trimethylsilyl)(methylthio)methane；tris(trimethylsilyl)methylthio-methane；Tris-(trimethylsilyl)-methylsulfid；Silane, ((methylthio)methylidyne)tris(trimethyl-；trimethyl-[methylsulfanyl-bis(trimethylsilyl)methyl]silane
• CAS: 31704-09-3
• 化学式: C₁₁H₃₀SSi₃
• 分子量: 278.682
• InChiKey: MVZAKYSSGMIRSP-UHFFFAOYSA-N

物化性质

• 沸点：
  255.2±40.0 °C(Predicted)
• 密度：
  0.841±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  tris(trimethylsilyl)methyl methyl sulfide 、 间氯过氧苯甲酸 以45%的产率得到
  参考文献：
  名称：

  RICCI A.; DEGLINNOCENTI A.; ANCILLOTTI M.; SECONI G.; DEMBECH P., TETRAHEDRON LETT., 27,(1986) N 49, 5985-5988

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲基二硫 、 tris(trimethylsilyl)methyllithium 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到tris(trimethylsilyl)methyl methyl sulfide
  参考文献：
  名称：

  Reactivity of the Triple Ion and Separated Ion Pair of Tris(trimethylsilyl)methyllithium with Aldehydes: A RINMR Study

  摘要：

  Low-temperature rapid-injection NMR (RINMR) experiments were performed on tris(trimethylsilyl) methyllithium. In THF/Me2O solutions, the separated ion (IS) reacted faster than can be measured at -130 degrees C with Mel and substituted benzaldehydes (k >= 2s(-1) whereas the contact ion (1C) dissociated to IS before reacting. Unexpectedly, the triple ion reacted faster with electron-rich benzaldehydes relative to electron-deficient ones. The addition of HMPA had no effect on the rate of reaction of the triple ion with p-diethylaminobenzaldehyde, and the immediate product of the reaction was the HMPA-solvated separated ion IS, with the Peterson product forming only slowly. Thus, the aldehyde is catalyzing the dissociation of the triple ion. HMPA greatly decelerated the reaction of IS (< 10(-10)), providing an estimate of the Lewis acid activating effect of a THF-solvated lithium cation in an organolithium addition to an aldehyde.

  DOI：

  10.1021/ja8003528

文献信息

• Sila pummerer rearrangement in highly sterically hindered organosilicon compounds: A new route to bis(trimethylsilyl)ketone
  作者：Alfredo Ricci、Alessandro Degl'Innocenti、Monica Ancillotti、Giancarlo Seconi、Pasquale Dembech

  DOI：10.1016/s0040-4039(00)85379-4

  日期：1986.1

  The oxidation of the tris(trimethylsi]yl)methylthio-methane with m-chloroperoxybenzoic acid, leads through a sila-Pummerer rearrangement occurring in unusually mild conditions, to bis(trimethylsilyl)ketone.

  用间氯过氧苯甲酸氧化三（三甲基甲硅烷基）甲硫基甲烷，会通过在异常温和的条件下发生的硅烷-Pummerer重排反应，生成双（三甲基甲硅烷基）酮。
• Bis (trimethylsilyl) thioketone
  作者：Alfredo Ricci、Alessandro Degl'Innocenti、Mariella Fiorenza、Pasquale Dembech、Nazmi Ramadan、Giancarlo Seconi、David R.M. Walton

  DOI：10.1016/s0040-4039(00)98520-4

  日期：1985.1
• Reactivity of the Triple Ion and Separated Ion Pair of Tris(trimethylsilyl)methyllithium with Aldehydes: A RINMR Study
  作者：Amanda C. Jones、Aaron W. Sanders、William H. Sikorski、Kristin L. Jansen、Hans J. Reich

  DOI：10.1021/ja8003528

  日期：2008.5.1

  Low-temperature rapid-injection NMR (RINMR) experiments were performed on tris(trimethylsilyl) methyllithium. In THF/Me2O solutions, the separated ion (IS) reacted faster than can be measured at -130 degrees C with Mel and substituted benzaldehydes (k >= 2s(-1) whereas the contact ion (1C) dissociated to IS before reacting. Unexpectedly, the triple ion reacted faster with electron-rich benzaldehydes relative to electron-deficient ones. The addition of HMPA had no effect on the rate of reaction of the triple ion with p-diethylaminobenzaldehyde, and the immediate product of the reaction was the HMPA-solvated separated ion IS, with the Peterson product forming only slowly. Thus, the aldehyde is catalyzing the dissociation of the triple ion. HMPA greatly decelerated the reaction of IS (< 10(-10)), providing an estimate of the Lewis acid activating effect of a THF-solvated lithium cation in an organolithium addition to an aldehyde.
• RICCI A.; DEGLINNOCENTI A.; ANCILLOTTI M.; SECONI G.; DEMBECH P., TETRAHEDRON LETT., 27,(1986) N 49, 5985-5988
  作者：RICCI A.、 DEGLINNOCENTI A.、 ANCILLOTTI M.、 SECONI G.、 DEMBECH P.

  DOI：——

  日期：——