[4-[(1S,6R,7S)-7-bicyclo[4.1.0]hept-2-enyl]-2-methylbut-3-yn-2-yl] 2,2-dimethylpropanoate | 1275615-71-8

• 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: [4-[(1S,6R,7S)-7-bicyclo[4.1.0]hept-2-enyl]-2-methylbut-3-yn-2-yl] 2,2-dimethylpropanoate
• CAS: 1275615-71-8
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: SXQSJVMLTDMSOU-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  [4-[(1S,6R,7S)-7-bicyclo[4.1.0]hept-2-enyl]-2-methylbut-3-yn-2-yl] 2,2-dimethylpropanoate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以82%的产率得到1-(propan-2-ylidene)-3a,4,5,7a-tetrahydro-1H-inden-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

文献信息

• Synthesis of Highly Functionalized Cyclohexenone Rings: Rhodium-Catalyzed 1,3-Acyloxy Migration and Subsequent [5+1] Cycloaddition
  作者：Dongxu Shu、Xiaoxun Li、Min Zhang、Patrick J. Robichaux、Weiping Tang

  DOI：10.1002/anie.201006881

  日期：2011.2.7

  from cyclopropyl‐substituted propargyl esters by using a [Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3‐acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the presence of CO with high regioselectivity.

  Lead Rh-ole：通过使用 [Rh(CO) 2 Cl} 2 ] 催化剂，由环丙基取代的炔丙酯制备高度取代的环己烯酮。这种金属催化剂在 CO 存在下促进了炔丙酯的 1,3-酰氧基迁移和随后得到的烯丙基环丙烷的 [5+1] 环加成反应，具有高区域选择性。