dimethyl 3-(4-methoxyphenyl)-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate | 1185881-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 3-(4-methoxyphenyl)-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
• 英文别名: dimethyl 3-(4-methoxyphenyl)-3,4-dihydro-1H-naphthalene-2,2-dicarboxylate
• CAS: 1185881-68-8
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: VRFWPOHAASWULE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-（2-（4-甲氧基苯基）乙炔基）苯甲醛 在 四氢呋喃 、 吡啶 、 10% palladium on activated carbon 、 氢气 、 四氯化钛 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 22.5h， 生成 dimethyl 3-(4-methoxyphenyl)-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
  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.