(3R,4S)-4-isobutyl-3-methyloxetan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S)-4-isobutyl-3-methyloxetan-2-one
• 英文别名: (3R,4S)-3-methyl-4-(2-methylpropyl)oxetan-2-one
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: UPZYMHDAWPFWPT-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (3R,4S)-4-isobutyl-3-methyloxetan-2-one 在 2-methyl-propan-2-ol; lanthanum tri-tert-butylate 作用下， 生成 (2R,3S)-3-Hydroxy-2,5-dimethyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene−Aldehyde Cycloadditions

  摘要：

  Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde.

  DOI：

  10.1021/ja0492900
• 作为产物：
  描述：

  丙酰氯 、 异戊醛 在 O-trimethylsilyl quinine 、 lithium perchlorate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以72%的产率得到(3R,4S)-4-isobutyl-3-methyloxetan-2-one
  参考文献：
  名称：

  Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene−Aldehyde Cycloadditions

  摘要：

  Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde.

  DOI：

  10.1021/ja0492900

文献信息

• Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene−Aldehyde Cycloadditions
  作者：Cheng Zhu、Xiaoqiang Shen、Scott G. Nelson

  DOI：10.1021/ja0492900

  日期：2004.5.1

  Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde.