2,6-Dioxa-bicyclo[5.2.0]non-1(7)-ene-8,9-dione | 61699-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-Dioxa-bicyclo[5.2.0]non-1(7)-ene-8,9-dione
• 英文别名: 2,6-Dioxabicyclo[5.2.0]non-1(7)-ene-8,9-dione
• CAS: 61699-85-2
• 化学式: C₇H₆O₄
• 分子量: 154.122
• InChiKey: UENHXZSHDQINTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-苄基-2-溴-N-甲基-2-丙烯-1-胺 、 1-bromo-6-methoxy-cyclohexene 、 2,6-Dioxa-bicyclo[5.2.0]non-1(7)-ene-8,9-dione 生成 (3aR*,5aS*,9S*,9aS*)-3a,4,5,5a,6,7,8,9-octahydro-3a-hydroxy-9-methoxy-4-methylene-1,1-(trimethylenedioxy)-3H-cyclopent[c]inden-3-one 、 (4bR,10aS,11aR)-10a-[(Benzyl-methyl-amino)-methyl]-4b-hydroxy-2,3,4b,7,8,10a,11,11a-octahydro-1H,6H-5,9-dioxa-indeno[1,2-a]azulen-10-one
  参考文献：
  名称：

  Evaluation of Amino Substituents as Nucleofugal Controllers of Regioselectivity and as Chelate Modulators of Stereoselectivity in Squarate Ester Cascades

  摘要：

  The tandem addition of an alkenyllithium reagent and a 2-lithioallylamine to squarate esters has been systematically examined. The effect of the sequencing of this twofold addition has been investigated. The extent to which the amino group is eliminated was found to be dependent on the structural features of the companion nucleophile. Also assessed was the comparative ease with which the amino and methoxy groups experience competitive beta-elimination from the highly reactive, medium-ring dianionic intermediates. Attempts were made to curtail the level of competing 1,4-addition, and success was achieved by increasing the effective size of the O-alkyl groups in the squarate ester. The highly stereocontrolled transformations described represent a notably direct means for producing highly fused polycyclic compounds, Mechanistic considerations sm rounding these reactions, which are characterized by an impressive enhancement of molecular scaffolding, are discussed.

  DOI：

  10.1021/jo9722919