2-cyclopropyl-6-((triisopropylsilyl)oxy)hex-3-yn-2-yl pivalate | 1392274-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyclopropyl-6-((triisopropylsilyl)oxy)hex-3-yn-2-yl pivalate
• 英文别名: [2-Cyclopropyl-6-tri(propan-2-yl)silyloxyhex-3-yn-2-yl] 2,2-dimethylpropanoate
• CAS: 1392274-84-8
• 化学式: C₂₃H₄₂O₃Si
• 分子量: 394.67
• InChiKey: FIMUKTNKXNNYCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-cyclopropyl-6-((triisopropylsilyl)oxy)hex-3-yn-2-yl pivalate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 50.0 ℃ 、1.01 MPa 条件下， 生成 (E)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)-3-((triisopropylsilyl)oxy)propyl pivalate 、 (Z)-1-(2-methyl-6-oxocyclohex-2-en-1-ylidene)-3-((triisopropylsilyl)oxy)propyl 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：

  but-3-ynyloxy-triisopropyl-silane 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 2-cyclopropyl-6-((triisopropylsilyl)oxy)hex-3-yn-2-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