2-oxo-1-(3-oxopentyl)cyclohexanecarboxylic acid ethyl ester

• 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: 2-oxo-1-(3-oxopentyl)cyclohexanecarboxylic acid ethyl ester
• 英文别名: ethyl 2-oxo-1-(3-oxopentyl)cyclohexane-1-carboxylate；ethyl 2-oxo-1-(3-oxopentyl)cyclohexanecarboxylate
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: QUDSLRBCXALSBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  2-环己烯-1-酮 、 2-环己酮甲酸乙酯 在 tris(pentafluoroethyl)difluorophosphorane 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以55%的产率得到2-oxo-1-(3-oxopentyl)cyclohexanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane

  摘要：

  Difluorotris(pentafluoroethyl)phosphorane, (C2F5)(3)PF2, was found to be an active catalyst for the Michael addition reaction of 1,3-beta-diketones or beta-ketoesters (Michael donors) and linear or cyclic unsaturated ketones (Michael acceptors). The reaction proceeds under mild conditions with low catalyst loading and results in the formation of the Michael addition products in moderate to high yields. The developed protocol does not require the use of a base for the in situ generation of a carbanion (Michael donor). (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.11.007

文献信息

• Electrochemically Induced Addition Reactions in the Absence of Solvent and Supporting Electrolyte
  作者：Tonino Caruso、Marta Feroci、Achille Inesi、Monica Orsini、Arrigo Scettri、Laura Palombi

  DOI：10.1002/adsc.200606082

  日期：2006.9

  Solvent- and supporting electrolyte-free electrolysis in a two-compartment cell proved to be effective for the direct electroactivation of CH acid-containing compounds vs. catalytic addition processes. Michael adducts (including quaternary carbon centres) and 2-nitroalkanols were obtained in very good yields and selectivity on application of a catalytic amount of electricity under galvanostatic conditions

  在两室电解槽中，无溶剂和无电解质的电解被证明对含CH酸的化合物的直接电活化相对于催化加成过程是有效的。通过在恒电流条件下施加催化量的电，可以非常好的收率和选择性获得迈克尔加合物（包括季碳中心）和2-硝基链烷醇。
• A New Method for the Preparation of Michael Adducts and Cyclic Enones Using Lithium Chloride-Hexamethylphosphoramide System.
  作者：Yutaka OZAKI、Ayako KUBO、Kyouko OKAMURA、Sang-Won KIM

  DOI：10.1248/cpb.43.734

  日期：——

  A new procedure using lithium chloride in hexamethylphosphoramide was found to be useful for the synthesis of Michael-type adducts and cyclic enones. Selectivity for the two products could be controlled by altering the reaction temperature employed. The urea-type solvents were also examined instead of hexamethylphosphoramide.

  一种使用氯化锂和六甲基磷酰胺的新程序被发现对迈克尔型加成物和环己烯酮的合成非常有用。通过改变反应温度，可以控制两种产品的选择性。此外，还研究了以脲类溶剂替代六甲基磷酰胺的情况。
• Silica gel-mediated catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to highly toxic methyl vinyl ketone without volatilization
  作者：Kiyoshi Tanemura、Taoufik Rohand

  DOI：10.1016/j.tetlet.2020.152142

  日期：2020.7

  Silica gel-mediated Michael addition of 1,3-dicarbonyl compounds to methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) was carried out to give the corresponding adducts in quite excellent yields. The reactions could be carried out without any catalysts and solvents. In addition, highly toxic MVK and EVK could be employed without significant volatilization. Silica gel could be recycled five times

  进行了硅胶介导的1,3-二羰基化合物到甲基乙烯基酮（MVK）和乙基乙烯基酮（EVK）的迈克尔加成反应，从而以相当优异的收率得到了相应的加合物。反应可以在没有任何催化剂和溶剂的情况下进行。此外，可以使用剧毒的MVK和EVK，而不会明显挥发。硅胶可以循环使用五次而不会降低产量。
• Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane
  作者：Bożena Bittner、Karsten Koppe、Walter Frank、Nikolai Ignat’ev

  DOI：10.1016/j.jfluchem.2015.11.007

  日期：2016.2

  Difluorotris(pentafluoroethyl)phosphorane, (C2F5)(3)PF2, was found to be an active catalyst for the Michael addition reaction of 1,3-beta-diketones or beta-ketoesters (Michael donors) and linear or cyclic unsaturated ketones (Michael acceptors). The reaction proceeds under mild conditions with low catalyst loading and results in the formation of the Michael addition products in moderate to high yields. The developed protocol does not require the use of a base for the in situ generation of a carbanion (Michael donor). (C) 2015 Elsevier B.V. All rights reserved.