| 134178-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• CAS: 134178-40-8；134178-41-9
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: UZAHYOJYNUMQMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-乙基-1-丁烯 、 3-[(E)-2-丁酰基]-1,3-噁唑烷-2-酮 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以3.5%的产率得到3-ethylidene-2,5-dimethylcyclohexan-1-one
  参考文献：
  名称：

  Lewis acid catalyzed ene reactions of .alpha.,.beta.-unsaturated N-acyloxazolidinones

  摘要：

  Chiral alpha,beta-unsaturated N-acyloxazolidinones undergo a variety of Lewis acid catalyzed addition reactions to alkenes with modest to excellent asymmetric induction. The nature of the reaction is a function of alkene structure and reaction conditions. N-Crotonyloxazolidinone 1b undergoes Me2AlCl-catalyzed ene reactions with methylenecyclopentane and allytrimethylsilane to give 6 (67% de) and 18 (33% de), respectively, as the major products. (Trimethylsilyl)cyclopentane 20 is formed stereospecifically as one of eight possible isomers as a minor product. Isobutylene undergoes an enantiospecific Me2AlCl-catalyzed hetero-Diels-Alder reaction with 1b to afford, after hydrolysis, lactone 10. 2-Ethyl-1-butene undergoes ene reaction slowly with 1b at -30-degrees-C with modest asymmetric induction. The ene adducts 6 and 11 undergo Me2AlCl-catalyzed Friedel-Crafts acylation at 0-degrees-C to give cyclohexenones 16 and 13. N-Acryloyloxazolidinones 21 and 26 undergo Me2AlCl-catalyzed ene reactions with 1,1-di- and trisubstituted alkenes to give ene adducts in excellent yield. However, asymmetric induction with ethylidenecyclohexane is poor, since ene reaction can occur by exo or endo transition states and by abstraction of syn or anti hydrogens. Ene reaction of 26 with (E)-3,4,4-trimethyl-2-pentene proceeds selectively through the exo transition state to give 28 with 80% de.

  DOI：

  10.1021/jo00016a019