1-(4-methoxybenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester | 1107060-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxybenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester
• CAS: 1107060-57-0
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: MVNGIGNFVVQEST-ZSOGYDGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester 、 C.I.酸性橙108 在 Montmorillonite KSF 作用下， 反应 0.05h， 以95%的产率得到1-(4-methoxybenzoyl)-cyclopropane-2,3-dicarboxylic acid bis[(2-hydroxyethyl)amide]
  参考文献：
  名称：

  Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds

  摘要：

  Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl beta-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable gamma-turn mimic scaffolds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.058
• 作为产物：
  描述：

  (E)-ethyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate 、 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以91%的产率得到1-(4-methoxybenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds

  摘要：

  Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl beta-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable gamma-turn mimic scaffolds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.058