1-Ethoxycarbonyl-1-(3-oxo-3-phenyl-propyl)-cyclopentanon-2 | 24740-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Ethoxycarbonyl-1-(3-oxo-3-phenyl-propyl)-cyclopentanon-2
• 英文别名: Ethyl 2-oxo-1-(3-oxo-3-phenylpropyl)cyclopentane-1-carboxylate
• CAS: 24740-29-2
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: HKFJTUQDRCFVTG-UHFFFAOYSA-N

物化性质

• 沸点：
  417.4±30.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Ethoxycarbonyl-1-(3-oxo-3-phenyl-propyl)-cyclopentanon-2 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 ethyl 8-oxo-4-phenylbicyclo[3.2.1]oct-3-ene-1-carboxylate
  参考文献：
  名称：

  铜催化双环[3]的不对称合成。n .1]烯酮

  摘要：

  一系列高应力双环[3。n .1]烯酮通过铜催化的正式[3 + 3]环加成反应，以良好至优异的对映选择性和中等至良好的收率成功构建。通用的手性环加合物可以选择性地转化成各种有价值的桥体系，对于构建含有[3]的天然和生物活性化合物具有巨大的潜力。Ñ 0.1]部分。

  DOI：

  10.1021/acs.joc.1c00146
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 、 3-二甲基氨基-1-苯丙烷-1-酮 在 氢氧化钾 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-Ethoxycarbonyl-1-(3-oxo-3-phenyl-propyl)-cyclopentanon-2
  参考文献：
  名称：

  The thermal michael reaction—III

  摘要：

  DOI：

  10.1016/s0040-4020(01)83053-2

文献信息

• Ytterbium triflate catalyzed Michael additions of β-ketoesters in water
  作者：Erik Keller、Ben L. Feringa

  DOI：10.1016/0040-4039(96)00141-4

  日期：1996.3

  Michael addition of various β-ketoesters towards enones and α,β-unsaturated aldehydes resulted in a quantitative conversion to the corresponding 1,4-adducts by performing the reactions in water in the presence of ytterbium triflate as a water-tolerant Lewis acid.

  在三氟甲磺酸y作为耐水的路易斯酸存在下，通过在水中进行反应，将各种β-酮酸酯迈克尔加成成烯酮和α，β-不饱和醛导致定量转化为相应的1,4-加合物。
• 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.
• New low-valent titanium reagents for dicarbonyl coupling and their use in a general method of annulation
  作者：Derrick L. J. Clive、Chengzhi Zhang、K. S. Keshava Murthy、William D. Hayward、Sylvain Daigneault

  DOI：10.1021/jo00022a042

  日期：1991.10

  New low-valent titanium reagents have been prepared by reducing TiCl3 (1 mol) with C8K (2 mol) or by reducing TiCl4 (1 mol) with Na-naphthalene (2.75 mol). Ketones carrying a chain that incorporates a suitably placed oxo function (aldehyde or ketone) undergo intramolecular dicarbonyl coupling to produce a bicyclic compound when treated with an excess (16-17 mol of titanium halide per mol of dicarbonyl compound) of one of these reagents. The procedure works well even for highly oxygenated substrates and constitutes a general method of annulation. Other reducing agents besides C8K or Na-naphthalene are suitable, and a brief examination of Na(Hg) and Na-K alloy was made. The C8K/TiCl3 system was also used to convert a cis-1,2-diol into the corresponding olefin.