[4-(Hydroxymethyl)-5-oxo-6-propan-2-ylidenecyclohexen-1-yl] 2,2-dimethylpropanoate | 1392274-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: [4-(Hydroxymethyl)-5-oxo-6-propan-2-ylidenecyclohexen-1-yl] 2,2-dimethylpropanoate
• CAS: 1392274-64-4
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: DOQUPIKXSUZDOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2,2-dimethyl-propionic acid 3-(2-hydroxymethyl-cyclopropyl)-1,1-dimethyl-prop-2-ynyl ester 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以79%的产率得到2,2-dimethyl-propionic acid 3-hydroxymethyl-6-isopropylidene-5-oxo-cyclohex-1-enyl ester
  参考文献：
  名称：

  Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition

  摘要：

  We have developed two different types of tandem reactions for the synthesis of highly functionalized cyclohexenones from cyclopropyl substituted propargyl esters. Both reactions were initiated by rhodium-catalyzed Saucy-Marbet 1,3-acyloxy migration. The resulting cyclopropyl substituted allenes derived from acyloxy migration then underwent [5 + 1] cycloaddition with CO. The acyloxy group not only eased the access to allene intermediates but also provided a handle for further selective functionalizations.

  DOI：

  10.1021/jo300973r