(S)-4-tert-butyl-oxetan-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: (S)-4-tert-butyl-oxetan-2-one
• 英文别名: (4S)-4-tert-butyloxetan-2-one
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: SJXFITPHLHUWTF-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  特戊醛 、 乙酰氯 在 TMS-quinidine 、 lithium perchlorate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以71%的产率得到(S)-4-tert-butyl-oxetan-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

• Asymmetric [2 + 2] cycloaddition of ketene with aldehydes catalysed by chiral bissulfonamide–trialkylaluminium complexes
  作者：Yasufumi Tamai、Hideki Yoshiwara、Masahiro Someya、Jun Fukumoto、Sotaro Miyano

  DOI：10.1039/c39940002281

  日期：——

  Asymmetric [2 + 2] cycloaddition of ketene with the aldehydes 1a–g, catalysed by 10 mol% of C2-symmetric bissulfonamide 2a–c–R3Al complexes afforded optically active 4-substituted oxetan-2-ones 3a–g in up to 74% enantiomeric excess.

  C2对称性双磺酰胺2a-c-R3Al络合物催化剂用量为10 mol%时，实现了与醛1a-g的不对称[2+2]环加成反应，合成了光学活性的4-取代氧杂环丁烷-2-酮3a-g，其对映体过量率高达74%。
• Practical Enantioselective Synthesis of β-Lactones Catalyzed by Aluminum Bissulfonamide Complexes
  作者：Thomas Kull、René Peters

  DOI：10.1002/adsc.200700084

  日期：2007.7.2

  practical aluminum-bissulfonamide complex catalyzed enantioselective formation of β-lactones by [2+2] cycloaddition of ketene (generated in situ from acetyl bromide by dehydrobromination) with various α-unbranched and -branched aliphatic aldehydes is presented. The methodology offers the advantage of operational simplicity not only as the ligand synthesis requires just a single sulfonylation step from commercially

  提出了一种有效和实用的铝-双磺酰胺铝配合物（通过乙烯酮的[2 + 2]环加成反应（由乙酰溴通过脱氢溴化而原位生成））与各种α-非支链和-支链的脂族醛催化β-内酯的对映选择性形成的研究。该方法提供了操作简单的优点，不仅因为配体合成仅需要来自市售对映体纯的二胺的单个磺酰化步骤。使用10摩尔％的双磺酰胺配体，可以高至极好的收率形成产品，其ee值通常在78％到90％之间。这项工作的关键发现是通过使用1.5：1的铝/配体比率来显着提高速率。
• 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.