(-)-(4R)-3-allyl-4-(1,1-difluoro-3-butenyl)-1,3-oxazolan-2-one | 364049-87-6

• 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)-3-allyl-4-(1,1-difluoro-3-butenyl)-1,3-oxazolan-2-one
• 英文别名: (4R)-4-(1,1-difluorobut-3-enyl)-3-prop-2-enyl-1,3-oxazolidin-2-one
• CAS: 364049-87-6
• 化学式: C₁₀H₁₃F₂NO₂
• 分子量: 217.216
• InChiKey: YROILKMQBIMAGI-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(4R)-3-allyl-4-(1,1-difluoro-3-butenyl)-1,3-oxazolan-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(-)-(9aR)-9,9-difluoro-5,8,9,9a-tetrahydro-1H-[1,3]oxazolo[3,4-a]azepin-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q
• 作为产物：
  描述：

  (-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.58h， 生成 (-)-(4R)-3-allyl-4-(1,1-difluoro-3-butenyl)-1,3-oxazolan-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q

文献信息

• Role of the <i>g</i><i>em</i>-Difluoro Moiety in the Tandem Ring-Closing Metathesis−Olefin Isomerization:  Regioselective Preparation of Unsaturated Lactams
  作者：Santos Fustero、María Sánchez-Roselló、Diego Jiménez、Juan F. Sanz-Cervera、Carlos del Pozo、José Luis Aceña

  DOI：10.1021/jo0525635

  日期：2006.3.31

  Careful selection of the metathesis catalyst, solvent, and reaction conditions allows for the efficient and regioselective synthesis of isomeric fluorinated and nonfluorinated lactam derivatives II and III from precursor amides I through a ring-closing metathesis (RCM) reaction or a tandem RCM−isomerization protocol, respectively. The presence of the gem-difluoro moiety in the starting materials exerts

  仔细选择复分解催化剂，溶剂和反应条件，可以通过闭环复分解（RCM）反应或串联RCM异构化协议从前体酰胺I高效且区域选择性地合成异构的氟化和非氟化内酰胺衍生物II和III。， 分别。起始物中的宝石-二氟部分的存在通过指导异构化步骤发挥关键作用，从而使整体串联转化成为区域选择性过程。还讨论了该协议的范围，局限性和综合实用性。
• Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Juan García Soler、Ana Bartolomé,、Amparo Asensio、Antonio Simón、Pierfrancesco Bravo、Giovanni Fronza、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/ol016087q

  日期：2001.8.1

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.