5-Ethenyl-3-methyloxolan-2-one | 478812-30-5

• 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: 5-Ethenyl-3-methyloxolan-2-one
• CAS: 478812-30-5
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: QWIPYNUIFLSAGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-methyl-4,5-dehydro ε-lactone 在 aluminum tris(2,6-diphenylphenoxide) 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 生成 5-Ethenyl-3-methyloxolan-2-one
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227

文献信息

• USE OF GAMMA-TOCOPHEROL AND ITS OXIDATIVE METABOLITE LLU-ALPHA IN THE TREATMENT OF DISEASE
  申请人：LOMA LINDA UNIVERSITY MEDICAL CENTER

  公开号：EP1140065A1

  公开（公告）日：2001-10-10
• EP1140065A4
  申请人：——

  公开号：EP1140065A4

  公开（公告）日：2002-10-16
• [EN] USE OF gamma -TOCOPHEROL AND ITS OXIDATIVE METABOLITE LLU- alpha IN THE TREATMENT OF DISEASE<br/>[FR] UTILISATION DU GAMMA-TOCOPHEROL ET DE SON METABOLITE OXYDATIF LLU-ALPHA DANS LE TRAITEMENT DE MALADIES
  申请人：UNIV LOMA LINDA MED

  公开号：WO2000035444A1

  公开（公告）日：2000-06-22

  The present invention is generally related to the discovery of teh therapeutic benefit of administering η-tocopherol and η-tocopherol derivatives. More specifically, the use of η-tocopherol and racemic LLU-α, (S)-LLU-α, or η-tocopherol derivatives as antioxidants and nitrogen oxide scavengers which treat and prevent high blood pressure, thromboembolic disease, cardiovascular disease, cancer, natriuretic disease, the formation of neuropathological lesions, and a reduced immune system response are disclosed.
• Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones
  作者：Emily B. Pentzer、Tendai Gadzikwa、SonBinh T. Nguyen

  DOI：10.1021/ol8022227

  日期：2008.12.18

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.