dimethyl 2-(3,5-dimethoxybenzylidene)malonate | 142944-05-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl 2-(3,5-dimethoxybenzylidene)malonate
• 英文别名: Dimethyl 2-(dimethoxybenzylidene)malonate；dimethyl 2-[(3,5-dimethoxyphenyl)methylidene]propanedioate
• CAS: 142944-05-6
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: FEYLTWLRUSIXJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(3,5-dimethoxybenzylidene)malonate 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 1.58h， 以67%的产率得到dimethyl 2-(3,5-dimethoxyphenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings

  摘要：

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

  DOI：

  10.1021/jo201612w
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 丙二酸二甲酯 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 以85%的产率得到dimethyl 2-(3,5-dimethoxybenzylidene)malonate
  参考文献：
  名称：

  (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings

  摘要：

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

  DOI：

  10.1021/jo201612w