dimethyl 2-methylnaphthalene-1,3-dicarboxylate | 1280677-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 2-methylnaphthalene-1,3-dicarboxylate
• 英文别名: Dimethyl 2-methylnaphthalene-1,3-dicarboxylate
• CAS: 1280677-88-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: PKIAWDKNANRNOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  乙酰乙酸甲酯 、 2-溴溴苄 在 2-吡啶甲酸 、 copper(l) iodide 、 caesium carbonate 作用下， 以 1-甲基吡咯烷 为溶剂， 反应 24.0h， 以65%的产率得到dimethyl 2-methylnaphthalene-1,3-dicarboxylate
  参考文献：
  名称：

  Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4H-Chromenes and Naphthalenes

  摘要：

  Depending on the ratio of the substrates and the reaction conditions, the Cu(I)-catalyzed domino reaction between bromobenzyl bromides and beta-ketoesters exclusively yields either 4H-chromenes or naphthalenes.

  DOI：

  10.1021/ol200347g

文献信息

• Cu(i)-catalyzed annulation for the synthesis of substituted naphthalenes using o-bromobenzaldehydes and β-ketoesters as substrates
  作者：Chandi C. Malakar、Kavitha Sudheendran、Hans-Georg Imrich、Sabine Mika、Uwe Beifuss

  DOI：10.1039/c2ob06963f

  日期：——

  Cu(I)-catalyzed reaction of o-bromobenzaldehydes with β-ketoesters using Cs2CO3 as a base and 2-picolinic acid as an additive proceeds under mild conditions and gives access to substituted naphthalenes in a single step with yields ranging from 71 to 86%. The new annulation process relies on a domino Knoevenagel condensation/C-arylation/1,2-addition/carboxylic acid cleavage. The annulation can also be achieved with o-iodobenzaldehyde.

  以 Cs2CO3 为碱和 2-吡啶甲酸为添加剂，Cu(I)催化邻溴苯甲醛与 δ 酮酯的反应在温和条件下进行，一步即可得到取代的萘，产率为 71% 至 86%。新的环化工艺依赖于多米诺 Knoevenagel 缩合/芳香化/1,2-加成/羧酸裂解。邻碘苯甲醛也可实现环化。
• Regioselective carboannulation of electron-deficient allenes with dialkyl (2-formylphenyl)malonates leading to multisubstituted naphthalenes
  作者：Nagaraju Koppanathi、K. C. Kumara Swamy

  DOI：10.1039/c6ob00787b

  日期：——

  An efficient base-catalysed regioselective carboannulation of allenoates (or allenylphosphonates) with dialkyl 2-(2-formylphenyl)malonates that leads to multi-substituted naphthalenes in high yields has been developed. This cascade reaction proceeds through Michael addition, cyclisation, dealkoxycarboxylation and tautomerisation. By using an allenylphosphine oxide, a species analogous to one of the

  已经开发了有效的碱催化的烯丙酸酯（或烯丙基膦酸酯）与2-（2-甲酰基苯基）丙二酸二烷基酯的区域选择性碳环化，其导致高产率的多取代萘。该级联反应通过迈克尔加成，环化，脱烷氧基羧化和互变异构进行。通过使用烯丙基膦氧化物，已经分离了类似于机械途径中的中间物种之一的物种。
• Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4<i>H</i>-Chromenes and Naphthalenes
  作者：Chandi C. Malakar、Dietmar Schmidt、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/ol200347g

  日期：2011.4.15

  Depending on the ratio of the substrates and the reaction conditions, the Cu(I)-catalyzed domino reaction between bromobenzyl bromides and beta-ketoesters exclusively yields either 4H-chromenes or naphthalenes.