(chloromethyl)triisopropylsilane

• 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: (chloromethyl)triisopropylsilane
• 英文别名: (Chloromethyl)triisopropylsilane；chloromethyl-tri(propan-2-yl)silane
• 化学式: C₁₀H₂₃ClSi
• 分子量: 206.831
• InChiKey: MDVVSUPFZHZUIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  12
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (chloromethyl)triisopropylsilane 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (tri-iso-propylsilyl)methylmagnesium chloride
  参考文献：
  名称：

  Palladium-catalyzed Kumada Coupling Reaction of Bromoporphyrins with Silylmethyl Grignard Reagents: Preparation of Silylmethyl-substituted Porphyrins as a Multipurpose Synthon for Fabrication of Porphyrin Systems

  摘要：

  We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbon-carbon single and double bonds.

  DOI：

  10.1021/jo302122f
• 作为产物：
  描述：

  (triisopropylsilyl)diazomethane 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以61%的产率得到(chloromethyl)triisopropylsilane
  参考文献：
  名称：

  Triisopropylsilyldiazomethane: A new stable reagent for esterification

  摘要：

  Triisopropylsilyldiazomethane (3), easily prepared in 96% yield from formyltriisopropylsilane tosythydrazone (2), undergoes smooth reaction with representative carboxylic acids to produce excellent yields of the corresponding silylmethyl esters (4).

  DOI：

  10.1016/s0040-4039(00)74042-1

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2018237194A1

  公开（公告）日：2018-12-27

  The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

  本公开内容提供了合成技术，包括用于立体选择性合成的试剂和方法。在某些实施例中，本公开内容提供了作为手性辅助剂有用的化合物。在某些实施例中，本公开内容提供了用于寡核苷酸合成的试剂和方法。在某些实施例中，本公开内容提供了用于手性控制寡核苷酸制备的试剂和方法。在某些实施例中，本公开内容的技术特别适用于构建具有挑战性的核苷酸间连接，提供高产率和立体选择性。
• Palladium-catalyzed Kumada Coupling Reaction of Bromoporphyrins with Silylmethyl Grignard Reagents: Preparation of Silylmethyl-substituted Porphyrins as a Multipurpose Synthon for Fabrication of Porphyrin Systems
  作者：Noriaki Sugita、Satoshi Hayashi、Fumio Hino、Toshikatsu Takanami

  DOI：10.1021/jo302122f

  日期：2012.12.7

  We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbon-carbon single and double bonds.
• Triisopropylsilyldiazomethane: A new stable reagent for esterification
  作者：John A. Soderquist、Edgar I. Miranda

  DOI：10.1016/s0040-4039(00)74042-1

  日期：1993.7

  Triisopropylsilyldiazomethane (3), easily prepared in 96% yield from formyltriisopropylsilane tosythydrazone (2), undergoes smooth reaction with representative carboxylic acids to produce excellent yields of the corresponding silylmethyl esters (4).