1-(tert-butyldiphenylsilyl)prop-2-en-1-ol | 1428137-64-7

• 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: 1-(tert-butyldiphenylsilyl)prop-2-en-1-ol
• 英文别名: 1-[Tert-butyl(diphenyl)silyl]prop-2-en-1-ol；1-[tert-butyl(diphenyl)silyl]prop-2-en-1-ol
• CAS: 1428137-64-7
• 化学式: C₁₉H₂₄OSi
• 分子量: 296.484
• InChiKey: KCHZCBKDTLMNPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-(tert-butyldiphenylsilyl)prop-2-en-1-ol 在 1,2-双(二苯基膦)乙烷氯化镍 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到1-(tert-butyldiphenylsilyl)propan-1-one
  参考文献：
  名称：

  Synthesis of Acylsilanes via Nickel-Catalyzed Reactions of α-Hydroxyallylsilanes

  摘要：

  The redox isomerization processes and tandem isomerization-aldolization reactions, mediated by nickel catalysts, offer new versatile entries to acylsilanes. For the second reaction, high diastereoselectivities, up to 98:2, have been obtained with bulky substituents on silicon.

  DOI：

  10.1021/ol4003064
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 丙烯醛 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 以40%的产率得到1-(tert-butyldiphenylsilyl)prop-2-en-1-ol
  参考文献：
  名称：

  Synthesis of Acylsilanes via Nickel-Catalyzed Reactions of α-Hydroxyallylsilanes

  摘要：

  The redox isomerization processes and tandem isomerization-aldolization reactions, mediated by nickel catalysts, offer new versatile entries to acylsilanes. For the second reaction, high diastereoselectivities, up to 98:2, have been obtained with bulky substituents on silicon.

  DOI：

  10.1021/ol4003064

文献信息

• α-Hydroxyallylsilanes as Propionaldehyde Enolate Equivalents and Their Use toward Iterative Aldol Reactions
  作者：Johal Ruiz、Akondi Srirama Murthy、Thierry Roisnel、Srivari Chandrasekhar、René Grée

  DOI：10.1021/acs.joc.5b00031

  日期：2015.2.20

  Smooth and efficient reaction conditions have been found for the transformation of protected beta-hydroxyacylsilanes into the corresponding aldehydes. This opens a new route to iterative aldol reactions, and it has been used for the synthesis of fragments of several bioactive natural products.
• Synthesis of Acylsilanes via Nickel-Catalyzed Reactions of α-Hydroxyallylsilanes
  作者：Gangireddy PavanKumar Reddy、J. Satyanarayana Reddy、Saibal Das、Thierry Roisnel、Jhillu S. Yadav、Srivari Chandrasekhar、René Grée

  DOI：10.1021/ol4003064

  日期：2013.4.5

  The redox isomerization processes and tandem isomerization-aldolization reactions, mediated by nickel catalysts, offer new versatile entries to acylsilanes. For the second reaction, high diastereoselectivities, up to 98:2, have been obtained with bulky substituents on silicon.