3-(dimethyl(phenyl)silyl)-1-(trimethylsilyl)pent-1-yn-3-ol | 918138-94-0

• 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: 3-(dimethyl(phenyl)silyl)-1-(trimethylsilyl)pent-1-yn-3-ol
• 英文别名: 3-[Dimethyl(phenyl)silyl]-1-(trimethylsilyl)pent-1-yn-3-ol；3-[dimethyl(phenyl)silyl]-1-trimethylsilylpent-1-yn-3-ol
• CAS: 918138-94-0
• 化学式: C₁₆H₂₆OSi₂
• 分子量: 290.553
• InChiKey: YKRKMUUIQBDPHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±32.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  19
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(dimethyl(phenyl)silyl)-1-(trimethylsilyl)pent-1-yn-3-ol 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  N-杂环卡宾引发的α-酰基乙烯基阴离子反应性：将α-羟基炔丙基硅烷添加到醛中。

  摘要：

  通过N-杂环卡宾引发的α-羟基炔丙基硅烷与醛的加成反应制备高度取代的α，β-不饱和酮。对于这些类型的化合物，该策略可作为标准Morita-Baylis-Hillman（MBH）方法的高效替代方案。与MBH反应相反，产物（R1）的β-位的不同取代可以以中等至优异的收率进行，并且高度控制所得的烯烃。

  DOI：

  10.1021/ol0710515
• 作为产物：
  描述：

  1-(二甲基(苯基)甲硅烷基)丙烷-1-酮 、 三甲基乙炔基硅 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以80%的产率得到3-(dimethyl(phenyl)silyl)-1-(trimethylsilyl)pent-1-yn-3-ol
  参考文献：
  名称：

  Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions

  摘要：

  Silyloxyallenes derived from alpha-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.

  DOI：

  10.1021/ja0653674

文献信息

• <i>N</i>-Heterocyclic Carbene-Initiated α-Acylvinyl Anion Reactivity:  Additions of α-Hydroxypropargylsilanes to Aldehydes
  作者：Troy E. Reynolds、Charlotte A. Stern、Karl A. Scheidt

  DOI：10.1021/ol0710515

  日期：2007.6.1

  Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated

  通过N-杂环卡宾引发的α-羟基炔丙基硅烷与醛的加成反应制备高度取代的α，β-不饱和酮。对于这些类型的化合物，该策略可作为标准Morita-Baylis-Hillman（MBH）方法的高效替代方案。与MBH反应相反，产物（R1）的β-位的不同取代可以以中等至优异的收率进行，并且高度控制所得的烯烃。
• Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions
  作者：Troy E. Reynolds、Ashwin R. Bharadwaj、Karl A. Scheidt

  DOI：10.1021/ja0653674

  日期：2006.12.1

  Silyloxyallenes derived from alpha-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.