(1R,2S,4S)-4-Benzyloxy-2-vinyl-cyclopentanecarboxylic acid methyl ester | 128261-52-9

• 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: (1R,2S,4S)-4-Benzyloxy-2-vinyl-cyclopentanecarboxylic acid methyl ester
• 英文别名: methyl (1R,2S,4S)-2-ethenyl-4-phenylmethoxycyclopentane-1-carboxylate
• CAS: 128261-52-9
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: GQFKKAZTTDAIBF-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(Benzyloxy)-2-ethenylcyclopropane 、 丙烯酸甲酯（MA） 在 偶氮二异丁腈 、 二苯二硫醚 作用下， 以 苯 为溶剂， 反应 0.75h， 生成 (1R,2R,4S)-4-Benzyloxy-2-vinyl-cyclopentanecarboxylic acid methyl ester 、 (1R,2R,4R)-4-Benzyloxy-2-vinyl-cyclopentanecarboxylic acid methyl ester 、 (1R,2S,4S)-4-Benzyloxy-2-vinyl-cyclopentanecarboxylic acid methyl ester 、 (1R,2S,4R)-4-Benzyloxy-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

文献信息

• Vinylcyclopentane synthesis via phenylthio radical catalyzed alkenylation of vinylcyclopropanes: preparative and mechanistic studies
  作者：Ken S. Feldman、Anthony L. Romanelli、Robert E. Ruckle、Ginette Jean

  DOI：10.1021/jo00027a020

  日期：1992.1

  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.