ethyl 5-methylene-2-oxo-bicyclo<2.2.2>octane-1-carboxylate | 133550-70-6

• 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: ethyl 5-methylene-2-oxo-bicyclo<2.2.2>octane-1-carboxylate
• 英文别名: Ethyl 5-methylidene-2-oxobicyclo[2.2.2]octane-1-carboxylate
• CAS: 133550-70-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CGUPYEYYHCZBOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 sodium tetrahydroborate 、 cerium(III) chloride 、 草酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 calcium carbonate 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 76.83h， 生成 ethyl 5-methylene-2-oxo-bicyclo<2.2.2>octane-1-carboxylate
  参考文献：
  名称：

  Vinyl radical cyclizations: synthesis of substituted bicyclooctanols

  摘要：

  The preparation and free-radical bicyclic ring closure of 4-(2-bromo-2-propen-1-yl)cyclohexene 7 is described. The bicyclo[3.2.1] and -[2.2.2] alcohols 9 and 10 arising, respectively, from 5-exo and 6-endo (or 6-exo) modes of cyclization of a vinyl radical were isolated in a 1:1 ratio. Factors affecting the regiochemical outcome were investigated.

  DOI：

  10.1021/jo00009a032

文献信息

• Vinyl radical cyclizations: synthesis of substituted bicyclooctanols
  作者：William F. Berkowitz、Phyllis J. Wilson

  DOI：10.1021/jo00009a032

  日期：1991.4

  The preparation and free-radical bicyclic ring closure of 4-(2-bromo-2-propen-1-yl)cyclohexene 7 is described. The bicyclo[3.2.1] and -[2.2.2] alcohols 9 and 10 arising, respectively, from 5-exo and 6-endo (or 6-exo) modes of cyclization of a vinyl radical were isolated in a 1:1 ratio. Factors affecting the regiochemical outcome were investigated.