diethyl 6-chloro-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate | 134260-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 6-chloro-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
• 英文别名: diethyl 6-chloro-3,4-dihydro-1H-naphthalene-2,2-dicarboxylate
• CAS: 134260-81-4
• 化学式: C₁₆H₁₉ClO₄
• 分子量: 310.777
• InChiKey: RUTBFUGGQMLYMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (4-chlorobenzyl)(2-iodoethyl)malonate 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 以59%的产率得到diethyl 6-chloro-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
  参考文献：
  名称：

  钯催化的成环芳族 C–H 烷基化与未活化的烷基卤化物

  摘要：

  描述了使用未活化的烷基卤化物和各种芳烃和杂芳烃的催化 CH 烷基化。这种成环过程适用于各种未活化的伯和仲烷基卤化物，包括具有 β-氢的那些。与芳香系统的标准极性或自由基环化相比，不需要底物的电子活化。温和的催化反应条件具有高度的官能团耐受性，有助于获得各种合成和医学上重要的碳环和杂环系统。

  DOI：

  10.1021/jacs.5b01365

文献信息

• Nickel-catalyzed, ring-forming aromatic C–H alkylations with unactivated alkyl halides
  作者：Quentin D. Tercenio、Erik J. Alexanian

  DOI：10.1016/j.tet.2019.05.047

  日期：2019.8

  alkylation of aromatic substrates with unactivated alkyl halides is described. This carbocyclization facilitates the synthesis of diverse fused ring systems from simple aromatic substrates and is an attractive alternative to traditional polar or radical-mediated ring formations. The present system uses unactivated primary and secondary alkyl bromides and chlorides, while avoiding the use of precious palladium

  描述了镍催化芳香族底物与未活化的烷基卤化物的 C-H 烷基化反应的发展。这种碳环化促进了从简单的芳香族底物合成多种稠合环系统，并且是传统极性或自由基介导的环形成的有吸引力的替代方案。本系统使用未活化的伯和仲烷基溴和氯化物，同时避免使用贵重的钯催化剂和相关C-H烷基化中常用的反应性更强的烷基卤。
• 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.