(4S)-3-(1'-oxo-2'-cyclopentenylethyl)-4-(1-methylethyl)-2-oxazolidinone | 192329-12-7

• 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: (4S)-3-(1'-oxo-2'-cyclopentenylethyl)-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: 2-Oxazolidinone, 3-(cyclopentylideneacetyl)-4-(1-methylethyl)-, (S)-；(4S)-3-(2-cyclopentylideneacetyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 192329-12-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: KDMLPNWVAKPYLE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (4S)-3-(1'-oxo-2'-cyclopentenylethyl)-4-(1-methylethyl)-2-oxazolidinone 在 三氟甲磺酸二丁硼 、 碘 、 碳酸氢钠 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 25.25h， 生成 (4S)-3-[(2S,3S,3aS,6aR)-3a-iodo-2-phenyl-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3-carbonyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Enantioselective Construction of Cyclic Ethers by An Aldol-Cyclization Sequence

  摘要：

  We have modified the substrate used in deconjugative aldol-cyclizations by incorporating the Evans chiral auxiliary. The deconjugative aldol step, using boron enolates, gave the expected products with complete syn-aldol stereochemistry. These compounds could then undergo an iodine-mediated cyclization to form optically active products. Oxetanes and fused ring tetrahydrofurans were easily assembled with a variety of substitution patterns and with excellent enantiocontrol. The deconjugation of acyclic chiral enimides resulted in the loss of control of olefin geometry. However, these compounds did appear to cyclize with excellent enantiocontrol.

  DOI：

  10.1021/jo961904z
• 作为产物：
  描述：

  环戊基乙酰氯 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以85%的产率得到(4S)-3-(1'-oxo-2'-cyclopentenylethyl)-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective Construction of Cyclic Ethers by An Aldol-Cyclization Sequence

  摘要：

  We have modified the substrate used in deconjugative aldol-cyclizations by incorporating the Evans chiral auxiliary. The deconjugative aldol step, using boron enolates, gave the expected products with complete syn-aldol stereochemistry. These compounds could then undergo an iodine-mediated cyclization to form optically active products. Oxetanes and fused ring tetrahydrofurans were easily assembled with a variety of substitution patterns and with excellent enantiocontrol. The deconjugation of acyclic chiral enimides resulted in the loss of control of olefin geometry. However, these compounds did appear to cyclize with excellent enantiocontrol.

  DOI：

  10.1021/jo961904z

文献信息

• Enantioselective Construction of Cyclic Ethers by An Aldol-Cyclization Sequence
  作者：Paul Galatsis、Scott D. Millan、George Ferguson

  DOI：10.1021/jo961904z

  日期：1997.7.1

  We have modified the substrate used in deconjugative aldol-cyclizations by incorporating the Evans chiral auxiliary. The deconjugative aldol step, using boron enolates, gave the expected products with complete syn-aldol stereochemistry. These compounds could then undergo an iodine-mediated cyclization to form optically active products. Oxetanes and fused ring tetrahydrofurans were easily assembled with a variety of substitution patterns and with excellent enantiocontrol. The deconjugation of acyclic chiral enimides resulted in the loss of control of olefin geometry. However, these compounds did appear to cyclize with excellent enantiocontrol.