Ethyl 2-oxo-1-(3-oxooctyl)cyclopentane-1-carboxylate | 917813-82-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2-oxo-1-(3-oxooctyl)cyclopentane-1-carboxylate
• 英文别名: ethyl 2-oxo-1-(3-oxooctyl)cyclopentane-1-carboxylate
• CAS: 917813-82-2
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: YQYMPWCIQLYOIP-UHFFFAOYSA-N

物化性质

• 沸点：
  387.1±27.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-辛烯-3-酮 、 2-氧代环戊羧酸乙酯 在 N,N-二乙基-N-甲基-N-(2-甲氧乙基)铵基双(三氟甲基磺酰)酰亚胺 、 iron(II) tetrafluoroborate hexahydrate 作用下， 反应 0.5h， 以86%的产率得到Ethyl 2-oxo-1-(3-oxooctyl)cyclopentane-1-carboxylate
  参考文献：
  名称：

  Development of Solvent-Driven Iron-Catalyzed Reactions

  摘要：

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.

  DOI：

  10.3987/rev-16-842

文献信息

• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.