(4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one | 866994-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(E,2R)-2-benzyl-5-trimethylsilylpent-3-enoyl]-1,3-oxazolidin-2-one
• CAS: 866994-20-9
• 化学式: C₂₅H₃₁NO₃Si
• 分子量: 421.612
• InChiKey: KSRUGOKADREQBA-UKRIWCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one 在 lithium hydroxide 、 lithium aluminium tetrahydride 、 双氧水 、 Selectfluor 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 64.0h， 生成 (2S,3S)-2-benzyl-3-fluoropent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of Novel Enantiopure Fluorinated Building Blocks from Acyclic Chiral Allylsilanes

  摘要：

  Homochiral,beta-fluorinated gamma,delta-unsaturated carboxylic acids with an allylic fluorinated stereogenic center are available from the corresponding enantiopure allylsilanes. The key step for introduction of the fluorine substituent is an electrophilic fluorodesilylation reaction carried out in the presence of Selectfluor. Reduction of the resulting beta-fluorinated pentenoic acid into the corresponding fluorinated alcohol was also performed leading to the formation of an enantiopure second-generation fluorinated building block.

  DOI：

  10.1021/ol0518535
• 作为产物：
  描述：

  (4R)-3-((E)-2-BUTENOYL)-4-(PHENYLMETHYL)-2-OXAZOLIDINONE 在 六甲基磷酰三胺 、 (Mes₂C₃H₅N₂)Cl₂Ru=CHPh 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 68.25h， 生成 (4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of Novel Enantiopure Fluorinated Building Blocks from Acyclic Chiral Allylsilanes

  摘要：

  Homochiral,beta-fluorinated gamma,delta-unsaturated carboxylic acids with an allylic fluorinated stereogenic center are available from the corresponding enantiopure allylsilanes. The key step for introduction of the fluorine substituent is an electrophilic fluorodesilylation reaction carried out in the presence of Selectfluor. Reduction of the resulting beta-fluorinated pentenoic acid into the corresponding fluorinated alcohol was also performed leading to the formation of an enantiopure second-generation fluorinated building block.

  DOI：

  10.1021/ol0518535

文献信息

• Fluorination process
  申请人：Gouverneur Veronique

  公开号：US20070142632A1

  公开（公告）日：2007-06-21

  Compounds of formula (II), (IIIa) or (IIIb) (variables are described in the specification) are prepared by fluorination of β,γ-unsaturated alkyl silanes. These compounds are useful as building blocks in the pharmaceutical industry.

  根据说明书中描述的变量，通过对β,γ-不饱和烷基硅烷进行氟化制备出式（II）、（IIIa）或（IIIb）的化合物。这些化合物在制药工业中作为构建模块非常有用。
• Synthesis of Novel Enantiopure Fluorinated Building Blocks from Acyclic Chiral Allylsilanes
  作者：Matthew Tredwell、Kenny Tenza、M Carmen Pacheco、Véronique Gouverneur

  DOI：10.1021/ol0518535

  日期：2005.9.1

  Homochiral,beta-fluorinated gamma,delta-unsaturated carboxylic acids with an allylic fluorinated stereogenic center are available from the corresponding enantiopure allylsilanes. The key step for introduction of the fluorine substituent is an electrophilic fluorodesilylation reaction carried out in the presence of Selectfluor. Reduction of the resulting beta-fluorinated pentenoic acid into the corresponding fluorinated alcohol was also performed leading to the formation of an enantiopure second-generation fluorinated building block.