diethyl 4-hexyl-5-methyl-3,4-dihydro-1H-naphthalene-2,2-dicarboxylate | 134261-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 4-hexyl-5-methyl-3,4-dihydro-1H-naphthalene-2,2-dicarboxylate
• CAS: 134261-05-5
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: UJZQPEJIOVWCPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  3-甲基苄溴 在 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 生成 diethyl 4-hexyl-5-methyl-3,4-dihydro-1H-naphthalene-2,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of substituted tetrahydronaphthalenes by manganese(III), cerium(IV), and iron(III) oxidation of substituted diethyl .alpha.-benzylmalonates in the presence of olefins

  摘要：

  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.

  DOI：

  10.1021/jo00018a023

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.