tert-butyl (1S,3R,4S)-3-(2,2-dimethylpropanoyloxy)-4-ethenylcyclopentane-1-carboxylate | 114127-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (1S,3R,4S)-3-(2,2-dimethylpropanoyloxy)-4-ethenylcyclopentane-1-carboxylate
• CAS: 114127-30-9
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: KXYUVOPEWSUOCD-FRRDWIJNSA-N

物化性质

• 沸点：
  338.6±42.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  新戊酸乙烯酯 、 1,1-Dimethylethyl 2-(1-Methylethenyl)cyclopropanecarboxylate 在 偶氮二异丁腈 、 三甲基铝 、 二苯二硫醚 作用下， 以 甲苯 为溶剂， 生成 tert-butyl (1S,3R,4S)-3-(2,2-dimethylpropanoyloxy)-4-ethenylcyclopentane-1-carboxylate 、 tert-butyl (1R,3R,4R)-3-(2,2-dimethylpropanoyloxy)-4-ethenylcyclopentane-1-carboxylate 、 tert-butyl (1S,3R,4R)-3-(2,2-dimethylpropanoyloxy)-4-ethenylcyclopentane-1-carboxylate
  参考文献：
  名称：

  通过自由基介导的官能化烯烃与取代乙烯基环丙烷的加成合成环戊烷

  摘要：

  Nouvelle strategie de synthese de cyclopentanes fonctionnalises grâce a l'addition catalysee par un Radical phenylthiyle d'alcenes substitues sur des cyclopropanesvinyliques substitues

  DOI：

  10.1021/ja00218a050

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.
• Cyclopentane synthesis via free radical mediated addition of functionalized alkenes to substituted vinyl cyclopropanes
  作者：Ken S. Feldman、Anthony L. Romanelli、Robert E. Ruckle、Raymond F. Miller

  DOI：10.1021/ja00218a050

  日期：1988.5

  Nouvelle strategie de synthese de cyclopentanes fonctionnalises grâce a l'addition catalysee par un radical phenylthiyle d'alcenes substitues sur des cyclopropanes vinyliques substitues

  Nouvelle strategie de synthese de cyclopentanes fonctionnalises grâce a l'addition catalysee par un Radical phenylthiyle d'alcenes substitues sur des cyclopropanesvinyliques substitues