3-tert-butyl-4-phenyloxetan-2-one | 186521-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-tert-butyl-4-phenyloxetan-2-one
• CAS: 186521-97-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: BSWKGJRIWUZRFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁酰氯 在 吡啶 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-tert-butyl-4-phenyloxetan-2-one
  参考文献：
  名称：

  A practical and efficient method for the synthesis of .beta.-lactones

  摘要：

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.

  DOI：

  10.1021/jo00003a047

文献信息

• Mulzer, Johann; Lammer, Ortrud, Angewandte Chemie, 1983, vol. 95, # 8, p. 629 - 630
  作者：Mulzer, Johann、Lammer, Ortrud

  DOI：——

  日期：——
• DANHEISER, RICK L.;NOWICK, JAMES S., J. ORG. CHEM., 56,(1991) N, C. 1176-1185
  作者：DANHEISER, RICK L.、NOWICK, JAMES S.

  DOI：——

  日期：——
• A practical and efficient method for the synthesis of .beta.-lactones
  作者：Rick L. Danheiser、James S. Nowick

  DOI：10.1021/jo00003a047

  日期：1991.2

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.