(1RS,12SR)-4-oxa-7,7-dimethylpentacyclo[10.6.1.0(3,11).0(5,10).0(13,18)]nonadeca-5(10),3(11),13,15,17-pentaen-9-one | 1126206-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1RS,12SR)-4-oxa-7,7-dimethylpentacyclo[10.6.1.0(3,11).0(5,10).0(13,18)]nonadeca-5(10),3(11),13,15,17-pentaen-9-one
• CAS: 1126206-26-5
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: NXFKRXBVLARMLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  Tricyclo<6.3.1.0^2,7>dodeca-2,4,6,9-tetraen 、 5,5-二甲基-1,3-环己二酮 在 copper(II) acetate monohydrate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 反应 4.0h， 以39%的产率得到(1SR,2RS,10RS,11RS,12SR)-3-oxa-6,6-dimethylpentacyclo[9.6.2.0(2,10).0(4,9).0(12,17)]nonadeca-4(9),12,14,16-tetraen-8-one
  参考文献：
  名称：

  Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies

  摘要：

  Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc)(3) in the presence of Cu(OAc)(2) in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular tandem oxidations were observed where unusually oxyl radicals attack the double bond to form the products. The mechanism of the formation of the products is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.012