5,7-Dioxapentacyclo[10.8.0.02,10.04,8.014,19]icosa-2,4(8),9,14,16,18-hexaen-11-one | 1185881-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5,7-Dioxapentacyclo[10.8.0.02,10.04,8.014,19]icosa-2,4(8),9,14,16,18-hexaen-11-one
• 英文别名: 5,7-dioxapentacyclo[10.8.0.02,10.04,8.014,19]icosa-2,4(8),9,14,16,18-hexaen-11-one
• CAS: 1185881-77-9
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: AFKGALOXJKVUHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-乙炔苯并[1,3]间二氧杂环戊烯 在 四氢吡咯 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 10% palladium on activated carbon 、 氢气 、 溶剂黄146 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙酸乙酯 、 甲苯 、 苯 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 96.5h， 生成 5,7-Dioxapentacyclo[10.8.0.02,10.04,8.014,19]icosa-2,4(8),9,14,16,18-hexaen-11-one
  参考文献：
  名称：

  Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

  摘要：

  Under Sc(OTf)(3) catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp(3)-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.007

文献信息

• Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids
  作者：Stuart J. Mahoney、David T. Moon、Jon Hollinger、Eric Fillion

  DOI：10.1016/j.tetlet.2009.06.007

  日期：2009.8

  Under Sc(OTf)(3) catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp(3)-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones. (C) 2009 Elsevier Ltd. All rights reserved.