10H-Phenanthrene-9,9-dicarboxylic acid diethyl ester | 118598-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 10H-Phenanthrene-9,9-dicarboxylic acid diethyl ester
• 英文别名: diethyl 10H-phenanthrene-9,9-dicarboxylate
• CAS: 118598-49-5
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: QZTVFDAQUAKLCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  在 indium 、 palladium 10% on activated carbon 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以61%的产率得到10H-Phenanthrene-9,9-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Palladium‐catalyzed Intramolecular Coupling Reactions between Vinyl Bromides, Aryl and Vinyl Halides, and Aryl Iodides Mediated by Indium: Preparation of Five‐ to Eight‐membered Carbocycles and Heterocycles

  摘要：

  DOI：

  10.1002/bkcs.10106

文献信息

• Synthesis of substituted tetrahydronaphthalenes by manganese(III), cerium(IV), and iron(III) oxidation of substituted diethyl .alpha.-benzylmalonates in the presence of olefins
  作者：Attilio Citterio、Roberto Sebastiano、Antonio Marion、Roberto Santi

  DOI：10.1021/jo00018a023

  日期：1991.8

  The oxidation of substituted diethyl alpha-benzylmalonates (1a-m) by manganese(III) acetate in acetic acid, cerium(IV) ammonium nitrate in methanol, or iron(III) perchlorate in acetonitrile in the presence of substituted olefins 2a-u was investigated. The results are consistent with a common mechanism. It involves selective generation of malonyl radicals from high-valent metal malonyl complexes, their addition to the olefin, and competition of the adduct radical between intramolecular cyclization to produce highly functionalized tetrahydronaphthalenes (3) and oxidation by metal salt to give mainly gamma-lactones (5). Several electron-withdrawing and releasing substituents on the aromatic ring and on the olefin can be successfully used in the synthesis of 3 without olefin telomerization. The influence of metal and olefin or aromatic substituents on the homolytic addition and intramolecular aromatic substitution is discussed.
• Manganese(III) acetate-induced cyclization of .alpha.-(arylalkyl) and .alpha.-(aryloxy)alkyl .beta.-dicarbonyl derivatives
  作者：Attilio Citterio、Daniele Fancelli、Claudia Finzi、Luca Pesce、Roberto Santi

  DOI：10.1021/jo00272a047

  日期：1989.5