(Z)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)propane-1,3-diyl bis(2,2-dimethylpropanoate) | 1392275-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)propane-1,3-diyl bis(2,2-dimethylpropanoate)
• 英文别名: [(3Z)-3-(2,2-dimethylpropanoyloxy)-3-(2-methyl-6-oxocyclohex-2-en-1-ylidene)propyl] 2,2-dimethylpropanoate
• CAS: 1392275-01-2
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: WQNDCUXRMROUTN-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-propionic acid but-3-ynyl ester 在 正丁基锂 、 di(rhodium)tetracarbonyl dichloride 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， -78.0~50.0 ℃ 、1.01 MPa 条件下， 反应 0.67h， 生成 (Z)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)propane-1,3-diyl bis(2,2-dimethylpropanoate) 、 (E)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)propane-1,3-diyl bis(2,2-dimethylpropanoate)
  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

文献信息

• Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition
  作者：Dongxu Shu、Xiaoxun Li、Min Zhang、Patrick J. Robichaux、Ilia A. Guzei、Weiping Tang

  DOI：10.1021/jo300973r

  日期：2012.8.3

  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.