(R)-5-Methyl-5-vinyl-dihydro-furan-2-one | 17152-14-6

• 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: (R)-5-Methyl-5-vinyl-dihydro-furan-2-one
• 英文别名: (5R)-5-ethenyl-5-methyloxolan-2-one
• CAS: 17152-14-6
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: QESPSAHXYXIGBG-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：

  (2S)-2-ethenyl-2-methylcyclobutan-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-5-Methyl-5-vinyl-dihydro-furan-2-one 、 (S)-5-methyl-5-ethenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  催化不对称瓦格纳-梅尔温变换。

  摘要：

  DOI：

  10.1021/ja010504c

文献信息

• Method for preparing 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-acetoxyromane-precursor- alpha-cehc precursor
  申请人：Spivak Anna Yulievna

  公开号：US20090306413A1

  公开（公告）日：2009-12-10

  The contemplated invention relates to the field of synthesis of biologically active substances, namely to the synthesis of an acetate derivative of the main water-soluble α-tocopherol metabolite known under the name of α-CEHC, which is prepared by the acid-catalyzed reaction of condensation of trimethyl hydroquinone with linalool in boiling octane, using n-toluenesulfonic acid or (+)-camphor-10-sulfonic acid as the catalyst. The reaction is carried out for 3 hours at the trimethyl hydroquinone:linalool:catalyst mole ratio of 1:1:0.1. The forming product is acetylated with acetic anhydride in pyridine at room temperature for 0.5 hour, and then ozonized in acetone in the presence of Ba(OH) 2 , oxidized with Jones' reagent in acetone, and isolated on silica gel column chromatography. Said compound is an acetate derivative of the main α-tocopherol metabolite—α-CEHC, for which high efficiency has been noted in treating disorders of the central nervous system.
• A Catalytic Asymmetric Wagner−Meerwein Shift
  作者：Barry M. Trost、Tatsuro Yasukata

  DOI：10.1021/ja010504c

  日期：2001.7.1