(R)-1-((1S,2S)-2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl)-6-phenylhex-2-yn-1-yl pivalate | 1392274-87-1

• 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: (R)-1-((1S,2S)-2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl)-6-phenylhex-2-yn-1-yl pivalate
• 英文别名: [(1R)-1-[(1S,2S)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl]-6-phenylhex-2-ynyl] 2,2-dimethylpropanoate
• CAS: 1392274-87-1
• 化学式: C₂₇H₃₈O₂
• 分子量: 394.598
• InChiKey: ORUIPPAKQRNCSK-DXBVXKBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (R)-1-((1S,2S)-2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl)-6-phenylhex-2-yn-1-yl pivalate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 生成 (Z)-(S)-1-(4-methyl-4-(4-methylpent-3-en-1-yl)-6-oxocyclohex-2-en-1-ylidene)-4-phenylbutyl pivalate 、 (E)-(S)-1-(4-methyl-4-(4-methylpent-3-en-1-yl)-6-oxocyclohex-2-en-1-ylidene)-4-phenylbutyl pivalate
  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
• 作为产物：
  描述：

  5-苯基-1-戊炔 、 (1S,2S)-2-methyl-2-(4-methylpent-3-enyl)cyclopropane-1-carbaldehyde 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 (R)-1-((1S,2S)-2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl)-6-phenylhex-2-yn-1-yl pivalate
  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.