fluoro(2-methylbut-3-enyl)diphenylsilane | 960315-75-7

• 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: fluoro(2-methylbut-3-enyl)diphenylsilane
• 英文别名: 3-methyl-4-(fluorodiphenylsilyl)-1-butene；Fluoro-(2-methylbut-3-enyl)-diphenylsilane；fluoro-(2-methylbut-3-enyl)-diphenylsilane
• CAS: 960315-75-7
• 化学式: C₁₇H₁₉FSi
• 分子量: 270.422
• InChiKey: FEEHBLNARYRCJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  fluoro(2-methylbut-3-enyl)diphenylsilane 在 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.5h， 生成 N-(diphenylmethylene)-1-[(2-methylbut-3-enyl)diphenylsilyl]-2-phenylethanamine
  参考文献：
  名称：

  Alpha-amino silanes via metalated imines as an approach to the synthesis of silanediol protease inhibitors

  摘要：

  Metalation of benzophenone imines for elaboration of the alpha-amino silane component of silanediol-based protease inhibitors allows for rapid diversification of targets. Coupling this chemistry with recently developed asymmetric hydrosilylation chemistry for preparing beta-silyl acids results in a streamlined process for drug design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.022
• 作为产物：
  描述：

  (3R,4R)-4-methyl-3-hydroxy-1,1-diphenylsilolane 在 氢氟酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以90%的产率得到fluoro(2-methylbut-3-enyl)diphenylsilane
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Silanediol Precursors from 1,5-Dihydrosiloles

  摘要：

  Dihydrosiloles are easily prepared from 1,3-dienes and dichlorosilanes, even on kilogram scale. Asymmetric hydroboration of a 3-alkyl-1,5-dihydrosilole, prepared from a 2-alkyl-1,3-diene, followed by treatment with aqueous HF results in Peterson fragmentation, forming optically active 3-alkyl-4-fluorosilyl-1-butenes. The fluorosilanes are stable to moisture but very reactive toward, nucleophiles. In addition, they can be converted to nucleophilic silyllithium reagents.

  DOI：

  10.1021/ol7021559

文献信息

• Alpha-amino silanes via metalated imines as an approach to the synthesis of silanediol protease inhibitors
  作者：Yingjian Bo、Paul B. Finn、Buddha B. Khatri、Scott McN. Sieburth

  DOI：10.1016/j.tet.2013.06.022

  日期：2013.9

  Metalation of benzophenone imines for elaboration of the alpha-amino silane component of silanediol-based protease inhibitors allows for rapid diversification of targets. Coupling this chemistry with recently developed asymmetric hydrosilylation chemistry for preparing beta-silyl acids results in a streamlined process for drug design. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient Asymmetric Synthesis of Silanediol Precursors from 1,5-Dihydrosiloles
  作者：Sushmita Sen、Madhusudhan Purushotham、Yingmei Qi、Scott McN. Sieburth

  DOI：10.1021/ol7021559

  日期：2007.11.1

  Dihydrosiloles are easily prepared from 1,3-dienes and dichlorosilanes, even on kilogram scale. Asymmetric hydroboration of a 3-alkyl-1,5-dihydrosilole, prepared from a 2-alkyl-1,3-diene, followed by treatment with aqueous HF results in Peterson fragmentation, forming optically active 3-alkyl-4-fluorosilyl-1-butenes. The fluorosilanes are stable to moisture but very reactive toward, nucleophiles. In addition, they can be converted to nucleophilic silyllithium reagents.