(3R,4S)-4-(dec-9-enyl)-3-methyloxetan-2-one | 652150-82-8

• 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-(dec-9-enyl)-3-methyloxetan-2-one
• 英文别名: (3R,4S)-4-(9-decenyl)-3-methyloxetan-2-one；(3R,4S)-4-(Dec-9-EN-1-YL)-3-methyloxetan-2-one；(3R,4S)-4-dec-9-enyl-3-methyloxetan-2-one
• CAS: 652150-82-8
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: SQBZVNBYBQUGNF-OLZOCXBDSA-N

物化性质

• 沸点：
  310.2±11.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-十一烯醛 、 丙酰氯 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74%的产率得到(3R,4S)-4-(dec-9-enyl)-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

• Catalyzed acyl halidealdehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions
  作者：Scott G. Nelson、Zhonghui Wan、Timothy J. Peelen、Keith L. Spencer

  DOI：10.1016/s0040-4039(99)01308-8

  日期：1999.9

  quantities (2.5–20 mol%) of Al(SbF6)3 catalyze the di(isopropyl)ethylamine-mediated cyclocondensation of various acyl halides and enolizable aldehydes to afford β-lactones in good yields (58–93%). These reactions are discussed as a strategy for executing chemo- and regiospecific catalyzed cross aldol reactions.

  Al（SbF 6）3的亚化学计量量（2.5–20 mol％）催化二（异丙基）乙胺介导的各种酰基卤和可烯醇化醛的环缩合反应，从而以高收率（58–93％）提供β-内酯。这些反应被讨论为执行化学和区域特异性催化的交叉羟醛缩合反应的策略。
• Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensation Reactions of Substituted Ketenes
  作者：Scott G. Nelson、Cheng Zhu、Xiaoqiang Shen

  DOI：10.1021/ja0391208

  日期：2004.1.1

  Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted beta-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional

  烷基取代的烯酮与结构不同的醛的催化不对称酰卤-醛环缩合 (AAC) 反应提供了具有高对映选择性的顺式双取代 β-内酯。AAC 反应利用一种新型的 Al(III)-三胺催化剂，其中金属的动态配位几何结构导致高度选择性的催化剂配合物。这些 AAC 反应代表了高度对映选择性取代的酯烯醇醇醛添加的功能解决方案。
• 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.