2,3-diisopropoxy-1-(5-methoxy-1-cyclopenten-1-yl)-6-methyl-2,5-heptadiene-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-diisopropoxy-1-(5-methoxy-1-cyclopenten-1-yl)-6-methyl-2,5-heptadiene-1,4-dione
• 英文别名: (2Z)-1-(5-methoxycyclopenten-1-yl)-6-methyl-2,3-di(propan-2-yloxy)hepta-2,5-diene-1,4-dione
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: ILRYIPMPAPHCOH-VXPUYCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 3,4-二异丙氧基-3-环丁烯-1,2-二酮 、 1-bromo-5-methoxycyclopentene 在 叔丁基锂 作用下， 生成 (3aR*,4S*,6aR*)-4,5,6,6a-tetrahydro-3a-hydroxy-2,3-diisopropoxy-4,6a-dimethyl-1-(3aH)-pentalenone 、 2,3-diisopropoxy-1-(5-methoxy-1-cyclopenten-1-yl)-6-methyl-2,5-heptadiene-1,4-dione
  参考文献：
  名称：

  Realization of Complete Regiochemical Control during the Conversion of Squarate Esters into Complex Linear and Angular Polyquinanes. The Consequences of Incorporating a Leaving Group into One of the Alkenyllithium Reactants

  摘要：

  A useful method is presented for controlling whether linear or angular triquinanes are formed during a reaction cascade initiated by the 2-fold addition of alkenyl anions to diisopropyl squarate, The key feature of the process involves the incorporation of a leaving group into one of the original nucleophilic reagents. Placement of the nucleofuge within a cyclic anion leads ultimately to formation of a linear product. Extracyclic and intracyclic options are possible, with preference given to the better leaving group when a competitive situation exists, When the leaving group is incorporated into an acyclic component, angular triquinanes result instead. Several other aspects of this impressive scaffolding scheme are detailed.

  DOI：

  10.1021/jo962181m

文献信息

• Realization of Complete Regiochemical Control during the Conversion of Squarate Esters into Complex Linear and Angular Polyquinanes. The Consequences of Incorporating a Leaving Group into One of the Alkenyllithium Reactants
  作者：Leo A. Paquette、Julien Doyon

  DOI：10.1021/jo962181m

  日期：1997.3.1

  A useful method is presented for controlling whether linear or angular triquinanes are formed during a reaction cascade initiated by the 2-fold addition of alkenyl anions to diisopropyl squarate, The key feature of the process involves the incorporation of a leaving group into one of the original nucleophilic reagents. Placement of the nucleofuge within a cyclic anion leads ultimately to formation of a linear product. Extracyclic and intracyclic options are possible, with preference given to the better leaving group when a competitive situation exists, When the leaving group is incorporated into an acyclic component, angular triquinanes result instead. Several other aspects of this impressive scaffolding scheme are detailed.