4746-97-8Relevant articles and documents
Studies on the synthesis of Schisandraceae natural products: Exploring a cyclopropylcarbinol ring expansion strategy
Fischer, Derek,Theodorakis, Emmanuel A.
, p. 4193 - 4196 (2007)
Acid mediated cyclopropylcarbinol ring expansion has been shown to be a viable method for the construction of the AB ring framework of lancifodilactone F and related terpenoids of the Schisandraceae family of natural products. We found that this rearrangement proceeds with good stereochemical control based on inversion of the C10 cyclopropyl center. Our studies indicate that the cis-decalin motif of 31 could be used as a key synthetic precursor of certain Schisandraceae metabolites. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis method of 1,4-cyclohexanedione monoethylene ketal
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Paragraph 0007; 0026; 0027; 0028; 0029; 0030, (2020/10/21)
The invention relates to the technical field of organic synthesis, and particularly discloses a synthesis method of 1,4-cyclohexanedione monoethylene ketal. The synthesis method comprises the following step: with dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate, ethylene glycol and water as raw materials and acidic ionic liquid as a reaction medium and a catalyst, sequentially carrying out heatingto 105-120 DEG C and 130-140 DEG C for reactions respectively to obtain the 1,4-cyclohexanedione monoethylene glycol ketal. According to the synthesis method disclosed by the invention, one-pot synthesis from dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate to 1,4-cyclohexanedione monoethylene glycol ketal is realized, and the problems of low industrial production efficiency and low yield of 1,4-cyclohexanedione monoethylene glycol ketal in the prior art are solved.
1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES
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Paragraph 0150; 0259-0260; 0262-0263, (2020/08/30)
The present disclosure relates to 1,5,7-trisubstituted isoquinoline derivatives, their preparation and pharmaceutical use. In particular, the present disclosure discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. The definitions of the groups in the formula can be found in the specification and claims.
Method for preparing 1,4-cyclohexanedione monoethylene glycol ketal
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Paragraph 0016-0021; 0023; 0024; 0026; 0027, (2019/04/04)
The invention relates to the technical field of chemical synthesis and particularly discloses a method for preparing 1,4-cyclohexanedione monoethylene glycol ketal. The method comprises the steps of producing an eutectic system from ammonium methyltriethylchloride and ethylene glycol, and then, directly adding 1,4-cyclohexanedione for a reaction. According to the method disclosed by the invention,produced monoketal is high in selectivity, the yield can reach 90% or more, and other reaction solvents are not required to be used, so that the production cost is reduced; after the reaction ends up, the product is easy to separate, and the operation is simple.
An investigation into the role of 2,6-lutidine as an additive for the RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones
Watson, David W.,Gill, Matthew,Kemmitt, Paul,Lamont, Scott G.,Popescu, Mihai V.,Simpson, Iain
supporting information, p. 4479 - 4482 (2018/11/23)
2,6-Lutidine has been identified as a beneficial additive for the oxidative cleavage of olefins to ketones by NaIO4 in the presence of catalytic RuCl3, improving the yield and shortening the reaction times. In the absence of 2,6-lutidine reactions stalled at the diol intermediate with incomplete conversion to the desired ketones. The reaction protocol described herein also avoids the use of harmful solvents such as CCl4 and DCE and is tolerant of a range of functional groups.
Alcohol Oxidations Using Reduced Polyoxovanadates
Campbell, McKenzie L.,Sulejmanovic, Dino,Schiller, Jacqueline B.,Turner, Emily M.,Hwu, Shiou-Jyh,Whitehead, Daniel C.
, (2017/03/20)
A full account of our recently communicated room temperature alcohol oxidation using reduced polyoxovanadates (r-POVs) is presented. Extensive optimizations revealed optimal conditions employing 0.02 equiv. of r-POV catalyst Cs5(V14As8O42Cl), 5 equiv. tert-butyl hydrogen peroxide (tBuOOH) as the terminal co-oxidant, in an acetone solvent for the quantitative oxidation of aryl-substituted secondary alcohols to their ketone products. The substrate scope tolerates most aryl substituted secondary alcohols in good to quantitative yields while alkyl secondary and primary activated alcohols were sluggish in comparison under similar conditions. Catalyst recyclability was successful on a 1.0?mmol scale of starting alcohol 1-phenylethanol. The oxidation was also successfully promoted by the VIV/VV mixed valent polyoxovanadate (POV) Cs11Na3Cl5(V15O36Cl). Finally, a third POV, Cs2.64(V5O9)(AsO4)2, was investigated for catalytic activity using our established reaction protocol, but proved ineffective as compared to the other two r-POV catalysts. This study expands the field of POM-mediated alcohol oxidations to include underexplored r-POV catalysts. While our catalysts do not supplant the best catalysts known for the transformation, their study may inform the development of other novel oxidative transformations mediated by r-POVs.
Oxidation of Secondary Methyl Ethers to Ketones
Gilissen, Pieter J.,Blanco-Ania, Daniel,Rutjes, Floris P. J. T.
, p. 6671 - 6679 (2017/07/15)
We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.
Hypervalent-Iodine-Mediated Formation of Epoxides from Carbon(sp2)-Carbon(sp3) Single Bonds
Jiang, Shan,Yan, Tai-Shan,Han, Yong-Chao,Cui, Li-Qian,Xue, Xiao-Song,Zhang, Chi
, p. 11691 - 11702 (2017/11/24)
We have developed an efficient method for direct formation of epoxide groups from carbon(sp2)-carbon(sp3) single bonds of β-keto esters; the reaction is mediated by the water-soluble hypervalent iodine(V) reagent AIBX (5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]iodoxol-1-ol anion). On the basis of the results of density functional theory calculations and experimental studies, we propose that the reaction proceeds by a two-stage mechanism involving dehydrogenation of the β-keto ester substrates and epoxidation of the resulting enone intermediates. The rate-limiting step is abstraction of the β′-C-H (calculated free energy of activation, 24.5 kcal/mol).
Room-temperature catalytic oxidation of alcohols with the polyoxovanadate salt Cs5(V14As8O42Cl)
Campbell, McKenzie L.,Sulejmanovic, Dino,Schiller, Jacqueline B.,Turner, Emily M.,Hwu, Shiou-Jyh,Whitehead, Daniel C.
, p. 3208 - 3213 (2016/05/24)
While many known methods for oxidation mediated by polyoxometalates (POMs) employ environmentally friendly co-oxidants, they tend to employ large catalyst loadings (e.g. 40 mol%) and costly high reaction temperatures (~90-135 °C) that potentially contribute to the degradation of the catalyst and reduce their effectiveness. Herein, we present some initial results demonstrating a room temperature catalytic oxidation using the reduced salt-inclusion polyoxometalate, Cs5(V14As8O42Cl), that contains polyoxovanadate (POV) clusters as an efficient catalyst (e.g., 2 mol%) in the transformation of secondary alcohols to their corresponding ketones in very good to quantitative yields. Further, the catalyst can be suspended on celite and recycled.
Method for the Production of Substituted and Unsubstituted Cyclohexanone Monoketals
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Page/Page column 4, (2010/09/05)
The invention relates to a novel process for preparing and isolating known substituted and unsubstituted 1,4-cyclohexanone monoketals.
