phenyl tripropylsilane | 78938-11-1

• 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: phenyl tripropylsilane
• 英文别名: phenyl(tri-n-propyl)silane；tripropylphenylsilane；Phenyl-tripropyl-silan；Phenyl-tripropyl-silane；phenyl(tripropyl)silane
• CAS: 78938-11-1
• 化学式: C₁₅H₂₆Si
• 分子量: 234.457
• InChiKey: PBWAWNMFKCRUCY-UHFFFAOYSA-N

物化性质

• 沸点：
  299.98°C (rough estimate)
• 密度：
  0.880

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2,2,2-trichloroethyl N-tosyloxycarbamate 、 phenyl tripropylsilane 在 [Rh2(O2CCPh3)4] 、 potassium carbonate 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以18%的产率得到
  参考文献：
  名称：

  β-硅效应促进的分子间位点选择性C（sp3）-H胺化与二价nitr腈。

  摘要：

  已经开发了有机硅化合物的-催化的β-选择性CH胺化反应。甲硅烷基乙基的伯C（sp3）-H键和硅环烷烃的仲C（sp3）-H键可以选择性地转化为硅原子β位的CN键。实验数据和理论计算表明，碳-硅键的强σ-供体能力是β-选择性的原因。动力学同位素效应清楚地表明，CH键的裂解步骤不是限制转换，而是决定选择性的步骤。

  DOI：

  10.1039/d0cc00959h
• 作为产物：
  描述：

  三丙基氯硅烷 、 苯基溴化镁 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到phenyl tripropylsilane
  参考文献：
  名称：

  β-硅效应促进的分子间位点选择性C（sp3）-H胺化与二价nitr腈。

  摘要：

  已经开发了有机硅化合物的-催化的β-选择性CH胺化反应。甲硅烷基乙基的伯C（sp3）-H键和硅环烷烃的仲C（sp3）-H键可以选择性地转化为硅原子β位的CN键。实验数据和理论计算表明，碳-硅键的强σ-供体能力是β-选择性的原因。动力学同位素效应清楚地表明，CH键的裂解步骤不是限制转换，而是决定选择性的步骤。

  DOI：

  10.1039/d0cc00959h

文献信息

• Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst
  作者：Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1021/jo8008148

  日期：2008.9.1

  We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-alpha, is also described.
• Intermolecular and Intramolecular, Platinum-Catalyzed, Acceptorless Dehydrogenative Coupling of Hydrosilanes with Aryl and Aliphatic Methyl C−H Bonds
  作者：Naofumi Tsukada、John F. Hartwig

  DOI：10.1021/ja050612p

  日期：2005.4.1

  Intermolecular acceptorless dehydrogenative coupling of silanes with arene C-H bonds and intramolecular coupling of silanes with aryl and alkyl C-H bonds occur in good yield in the presence of 5 mol % of TpMe2PtMe2H (TpMe2 = hydridotris(3,5-dimethylpyrazolyl)borate) and related platinum(IV) complexes. The intermolecular reactions of arenes occurred with both trialkyl and dialkylaryl silanes. Intramolecular reactions of dialkylsilylalkylarenes occurred at aryl C-H bonds, and reactions of tributylsilane or dibutylphenylsilane occurred intramolecularly at the aliphatic, primary C-H bond. The reactions of arenes occurred preferentially at the least sterically hindered C-H bonds and preferentially with more electron-poor arenes. Crossover experiments and the lack of reactivity of the arylsilanes with H2 imply that the dehydrogenative silylation of arenes can be irreversible, even in a closed reaction vessel.
• Toptschiew et al., Doklady Akademii Nauk SSSR, 1958, vol. 118, p. 731,732
  作者：Toptschiew et al.

  DOI：——

  日期：——
• Metallosiloxanes containing period 5 transition metals: synthesis and X-ray studies of three cadmium siloxanes
  作者：Natalia V. Sergienko、Alexander A. Korlyukov、Dmitry E. Arkhipov、Valentin V. Novikov、Marina A. Eskova、Boris G. Zavin

  DOI：10.1016/j.mencom.2016.07.026

  日期：2016.7

  Hydrolysis of PhSi(OEt)(3) in the presence of MOH (M = K, Na) and CdBr2 affords new cadmium siloxanes of sandwich type, whose encapsulated species (Br-, H2O, OH) are defined by the solvent used for synthesis and crystallization.
• β-Silicon-effect-promoted intermolecular site-selective C(sp³)–H amination with dirhodium nitrenes
  作者：Ryo Ninomiya、Kenta Arai、Gong Chen、Kazuhiro Morisaki、Takeo Kawabata、Yoshihiro Ueda

  DOI：10.1039/d0cc00959h

  日期：——

  A dirhodium-catalyzed, β-selective C-H amination of organosilicon compounds has been developed. Primary C(sp3)-H bonds of silylethyl groups and secondary C(sp3)-H bonds of silacycloalkanes can be selectively converted to C-N bonds at the β-position of the silicon atoms. The experimental data and theoretical calculations indicate that the strong σ-donor ability of the carbon-silicon bonds is responsible

  已经开发了有机硅化合物的-催化的β-选择性CH胺化反应。甲硅烷基乙基的伯C（sp3）-H键和硅环烷烃的仲C（sp3）-H键可以选择性地转化为硅原子β位的CN键。实验数据和理论计算表明，碳-硅键的强σ-供体能力是β-选择性的原因。动力学同位素效应清楚地表明，CH键的裂解步骤不是限制转换，而是决定选择性的步骤。