ethyl 2-oxo-1-(3-oxopentyl)cyclopentane-1-carboxylate | 176101-58-9

• 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-oxopentyl)cyclopentane-1-carboxylate
• 英文别名: 2-ethoxycarbonyl-2-(3-oxopentyl)cyclopentanone；Ethyl 2-oxo-1-(3-oxopentyl)cyclopentane-1-carboxylate
• CAS: 176101-58-9
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: CTOFCZPSQYLEKW-UHFFFAOYSA-N

物化性质

• 沸点：
  343.3±27.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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-戊烯-3-酮 、 2-氧代环戊羧酸乙酯 在 ytterbium(III) triflate 作用下， 反应 120.0h， 生成 ethyl 2-oxo-1-(3-oxopentyl)cyclopentane-1-carboxylate
  参考文献：
  名称：

  三氟甲磺酸催化水中β-酮酸酯的迈克尔加成

  摘要：

  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。

  DOI：

  10.1016/0040-4039(96)00141-4

文献信息

• Heterogeneous Amine Catalyst Grafted on Amorphous Silica: An Effective Organocatalyst for Microwave-promoted Michael Reaction of 1,3-Dicarbonyl Compounds in Water
  作者：Hisahiro Hagiwara、Sachiyo Inotsume、Masakazu Fukushima、Takashi Hoshi、Toshio Suzuki

  DOI：10.1246/cl.2006.926

  日期：2006.8

  Michael addition of a 1,3-dicarbonyl compound to an α,β-unsaturated carbonyl compound was effectively catalyzed by heterogeneous N,N-diethylaminopropylated silica gel (NDEAP) in water under microwave heating. The reaction condition was mild, practical, and environmentally benign. The sustainable nature of the catalyst was exemplified by re-use up to 5 times.

  在微波加热下，于水中，N,N-二乙基氨基丙基化硅胶（NDEAP）有效地催化1,3-二羰基化合物与α,β-不饱和羰基化合物的迈克尔加成反应。反应条件温和、实用且环境友好。催化剂的可持续性通过重复使用多达5次得以体现。
• 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。
• Monomeric Metal Aqua Complexes in the Interlayer Space of Montmorillonites as Strong Lewis Acid Catalysts for Heterogeneous Carbon-Carbon Bond-Forming Reactions
  作者：Tomonori Kawabata、Masaki Kato、Tomoo Mizugaki、Kohki Ebitani、Kiyotomi Kaneda

  DOI：10.1002/chem.200400672

  日期：2005.1

  scandium catalysts (Cu(2+)- and Sc(3+)-monts) were easily prepared by treating Na(+)-mont with the aqueous solution of the copper nitrate and scandium triflate, respectively. The resulting Cu(2+)- and Sc(3+)-monts showed outstanding catalytic activities for a variety of carbon-carbon bond-forming reactions, such as the Michael reaction, the Sakurai-Hosomi allylation, and the Diels-Alder reaction, under

  蒙脱土包裹的铜和scan催化剂（Cu（2 +）-和Sc（3 +）-monts）可以通过分别用硝酸铜和三氟甲磺酸scan的水溶液处理Na（+）-mont来轻松制备。所得的Cu（2 +）-和Sc（3 +）-monts对各种碳-碳键形成反应（例如Michael反应，Sakurai-Hosomi烯丙基化和Diels-Alder反应）表现出出色的催化活性在无溶剂或水性条件下使用。蒙特催化剂的显着活性归因于能够稳定金属阳离子的带负电荷的硅酸盐层。此外，这些催化剂可重复使用，而活性和选择性没有任何明显的损失。Cu（2 +）-mont催化的Michael反应通过三元复合物进行，其中1和2
• Creation of monomeric La complexes on apatite surfaces and their application as heterogeneous catalysts for Michael reactions
  作者：Kohsuke Mori、Michitaka Oshiba、Takayoshi Hara、Tomoo Mizugaki、Kohki Ebitani、Kiyotomi Kaneda

  DOI：10.1039/b512030f

  日期：——

  Using a cation-exchange method, an equimolar substitution of La3+ for Ca2+ occurred by the treatment of stoichiometric hydroxyapatite (HAP: Ca10(PO4)6(OH)2) with an aqueous solution of La(OTf)3, affording a monomeric hydroxyapatite-bound La complex (LaHAP). Physicochemical characterization by means of XRD, XPS, IR, and La K-edge XAFS analyses proved that a monomeric La3+ phosphate complex was generated on its surface. Such monomeric La3+ species function as an efficient heterogeneous catalyst for the Michael reaction of 1,3-dicarbonyls with enones under aqueous or solvent-free conditions. The work-up procedure is straightforward and the spent catalyst could be recycled without any loss of the catalytic activity. Further application to an asymmetric version was also investigated using various apatite catalysts modified with chiral organic ligands. Enantioselectivity was found to depend on the chiral ligand, solvent, and rare earth metal triflate precursor (RE(OTf)3) for the reaction of methyl 1-oxoindan-2-carboxylate with methyl vinyl ketone. Under optimized reaction conditions, a monomeric fluoroapatite-bound La complex catalyst modified with (R,R)-tartaric acid (TA-LaFAP) provided the Michael adduct quantitatively in up to 60% ee.

  采用阳离子交换法，通过将化学计量的羟基磷灰石（HAP：Ca\(}_10}\)(PO\(}_4}\))\(}_6}\)(OH)\(}_2}\)）与La(OTf)\(}_3}\)的水溶液处理，实现了La\(}^3+}\)对Ca\(}^2+}\)的等摩尔取代，得到了单体羟基磷灰石结合的镧配合物（LaHAP）。通过XRD、XPS、IR和La K边XAFS分析的物理化学表征证明，在其表面生成了单体La\(}^3+}\)磷酸盐配合物。这种单体La\(}^3+}\)物种作为高效的非均相催化剂，在水相或无溶剂条件下对1,3-二羰基化合物与烯酮的迈克尔加成反应具有催化作用。后处理过程简单，且催化剂可回收，无催化活性损失。此外，还研究了通过各种含手性有机配体的磷灰石催化剂的进一步应用，以实现不对称版本。在甲基1-氧茚-2-羧酸酯与甲基乙烯基酮的反应中，产物的对映选择性取决于手性配体、溶剂和稀土金属三氟甲磺酸盐前体（RE(OTf)\(}_3}\)）。在优化的反应条件下，经过(R,R)-酒石酸（TA-LaFAP）修饰的单体氟磷灰石结合的镧配合物催化剂，能使迈克尔加成产物达到定量收率，最高对映体过量值达60%。
• Michael reaction of 1,3-dicarbonyls with enones catalyzed by a hydroxyapatite-bound La complex
  作者：Kohsuke Mori、Michitaka Oshiba、Takayoshi Hara、Tomoo Mizugaki、Kohki Ebitani、Kiyotomi Kaneda

  DOI：10.1016/j.tetlet.2005.04.099

  日期：2005.6

  A hydroxyapatite-bound La complex, which functioned as an efficient heterogeneous catalyst for the Michael reaction of 1.3-dicarbonvis with enones under aqueous or solvent-free conditions, was prepared using a cation-exchange method. Further application to an asymmetric version by a fluoroapatite-bound La complex catalyst modified with (R,R)-tartaric acid is also described. (c) 2005 Elsevier Ltd. All rights reserved.