(2RS,3SR)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2,4,4-trimethylpentan-1-one

• 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: (2RS,3SR)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2,4,4-trimethylpentan-1-one
• 英文别名: (syn)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2,4,4-trimethylpentan-1-one；(2R,3R)-1-[tert-butyl(diphenyl)silyl]-3-hydroxy-2,4,4-trimethylpentan-1-one
• 化学式: C₂₄H₃₄O₂Si
• 分子量: 382.618
• InChiKey: XFTIIYJGTBHMIP-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2,4,4-trimethylpentan-1-one 、 对溴苯甲醛 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 以81%的产率得到(1RS,2SR,3SR)-1-(4-bromophenyl)-3-(tert-butyldiphenylsilyl)-3-hydroxy-2-methylpropyl 4-bromobenzoate
  参考文献：
  名称：

  Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes

  摘要：

  Three complementary strategies have been explored to obtain stereodefined 1,3 diols starting from easily accessible syn beta-hydroxy acylsilanes: fluoride induced migrations of substituents on silicon, a Grignard addition followed by protodesilylation and Tischenko-type reactions. Preliminary data on scope and limitations of these processes are presented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.034
• 作为产物：
  描述：

  (syn)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 、 特戊醛 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 以40%的产率得到(2RS,3SR)-1-(tert-butyldiphenylsilyl)-3-hydroxy-2,4,4-trimethylpentan-1-one
  参考文献：
  名称：

  Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes

  摘要：

  Three complementary strategies have been explored to obtain stereodefined 1,3 diols starting from easily accessible syn beta-hydroxy acylsilanes: fluoride induced migrations of substituents on silicon, a Grignard addition followed by protodesilylation and Tischenko-type reactions. Preliminary data on scope and limitations of these processes are presented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.034

文献信息

• 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.
• Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes
  作者：Gangireddy PavanKumar Reddy、Akondi Srirama Murthy、J. Satyanarayana Reddy、Saibal Das、Thierry Roisnel、Jhillu S. Yadav、Srivari Chandrasekhar、René Grée

  DOI：10.1016/j.tetlet.2013.11.034

  日期：2014.1

  Three complementary strategies have been explored to obtain stereodefined 1,3 diols starting from easily accessible syn beta-hydroxy acylsilanes: fluoride induced migrations of substituents on silicon, a Grignard addition followed by protodesilylation and Tischenko-type reactions. Preliminary data on scope and limitations of these processes are presented. (C) 2013 Elsevier Ltd. All rights reserved.