5-(2-(4-(dimethylamino)phenethyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 1185881-53-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-(2-(4-(dimethylamino)phenethyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[[2-[2-[4-(Dimethylamino)phenyl]ethyl]phenyl]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[[2-[2-[4-(dimethylamino)phenyl]ethyl]phenyl]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1185881-53-1
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: HJLHQYOGCZTFAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-(4-(dimethylamino)phenethyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以63%的产率得到3'-(4-(dimethylamino)phenyl)-2,2-dimethyl-3',4'-dihydro-1'H-spiro[[1,3]dioxane-5,2'-naphthalene]-4,6-dione
  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
• 作为产物：
  描述：

  (2-methoxycarbonylbenzyl)triphenylphosphonium bromide 在 四氢吡咯 、 10% palladium on activated carbon 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 、 苯 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 5-(2-(4-(dimethylamino)phenethyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  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.