(1S,2S)-4,4-Dimethoxy-2-vinyl-cyclopentanecarboxylic acid methyl ester | 137144-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-4,4-Dimethoxy-2-vinyl-cyclopentanecarboxylic acid methyl ester
• CAS: 137144-96-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: GMBCFRVBDQXWIA-BDAKNGLRSA-N

物化性质

• 沸点：
  242.0±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  1,1-Dimethoxy-2-ethenylcyclopropane 、 丙烯酸甲酯（MA） 在 偶氮二异丁腈 、 三甲基铝 、 二苯二硫醚 作用下， 以 苯 为溶剂， 反应 2.25h， 生成 (1S,2R)-4,4-Dimethoxy-2-vinyl-cyclopentanecarboxylic acid methyl ester 、 (1S,2S)-4,4-Dimethoxy-2-vinyl-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Vinylcyclopentane synthesis via phenylthio radical catalyzed alkenylation of vinylcyclopropanes: preparative and mechanistic studies

  摘要：

  1-Vinylcyclopropanes bearing ether or ester substituents at C(2) of the cyclopropyl ring or alkyl groups at other ring (or alkenyl) positions were subjected to PhS. catalyzed olefination with ester- or oxygen-functionalized alkenes. In some instances, variations in reaction conditions (low temperature, Lewis acids) led to levels of stereoselectivity unprecedented in such simple, unbiased substrates. In general, the stereochemical outcome of these transformations can be rationalized by citing existing models for selectivity upon cyclization of substituted 5-hexenyl radicals. However, in a few specific instances, results obtained with alkylated vinylcyclopropyl substrates are not consistent with some of the predictions of these models.

  DOI：

  10.1021/jo00027a020