- Method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in continuous flow microreactor
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The invention relates to a method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in a continuous flow microreactor, which comprises the following steps: (1) uniformly mixing a compound 1 and a compound 2 to obtain a homogeneous phase solution A; (2) uniformly mixing aluminum trichloride, a compound 1 and an organic solvent to obtain a homogeneous phase solution B; (3) diluting concentrated hydrochloric acid with water to prepare a solution C; and (4) transferring the homogeneous phase solution A and the homogeneous phase solution B into a first micro-reaction module for a Friedel-Crafts acylation reaction, after the reaction is finished, transferring the obtained reaction solution and the solution C into a second micro-reaction module for quenching reaction, and then performing liquid separation, washing and vacuum concentration to obtain a target compound 3; wherein the specific synthesis route is as follows. By adopting the method disclosed by the invention, the target product can be continuously and rapidly synthesized, aluminum trichloride is not needed for treatment, the reaction condition is mild, the reaction time is short, and the yield is high and reaches 90% or above.
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Paragraph 0053-0058
(2021/05/12)
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- Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones
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A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.
- Xin, Hong,Duan, Xin-Hua,Yang, Mingyu,Zhang, Yiwen,Guo, Li-Na
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p. 8263 - 8273
(2021/06/30)
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- Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones
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A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.
- Hua, Yun-Yu,Bin, Huai-Yu,Wei, Tao,Cheng, Hou-An,Lin, Zu-Peng,Fu, Xing-Feng,Li, Yuan-Qiang,Xie, Jian-Hua,Yan, Pu-Cha,Zhou, Qi-Lin
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supporting information
p. 818 - 822
(2020/02/15)
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- Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation
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A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
- Estopi?á-Durán, Susana,Donnelly, Liam J.,Mclean, Euan B.,Hockin, Bryony M.,Slawin, Alexandra M. Z.,Taylor, James E.
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supporting information
p. 3950 - 3956
(2019/02/16)
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- Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids
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A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.
- Duhamel, Thomas,Mu?iz, Kilian
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supporting information
p. 933 - 936
(2019/01/23)
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- Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
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Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
- Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
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supporting information
p. 16490 - 16494
(2019/11/03)
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- Visible-Light-Promoted Metal-Free Aerobic Oxidation of Primary Amines to Acids and Lactones
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A unique metal-free aerobic oxidation of primary amines via visible light photocatalytic double carbon–carbon bonds cleavage and multi carbon–hydrogen bonds oxidation was observed. Aerobic oxidation of primary amines could be controlled to afford acids by using dioxane with 18 W CFL, and lactones by using DMF with 8 W green LEDs, respectively. A plausible mechanism was proposed based on control experiments. This observation showed direct evidences for the fragmentation in the aerobic oxidation of aliphatic primary amines.
- Cheng, Xiaokai,Yang, Bo,Hu, Xingen,Xu, Qing,Lu, Zhan
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p. 17566 - 17570
(2016/11/29)
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- Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: Enantioselective synthesis of (+)-Centrolobine
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An efficient asymmetric hydrogenation of δ-keto Weinreb amides catalyzed by a Ru-Xyl-SunPhos-Daipen bifunctional catalyst has been achieved. This method afforded a series of enantio-enriched δ-hydroxy Weinreb amides in good yields (up to 93%) and enantioselectivities (up to 99%). This protocol was successfully applied to the synthesis of the key intermediate of (+)-Centrolobine.
- Zhao, Mengmeng,Lu, Bin,Ding, Guangni,Ren, Kai,Xie, Xiaomin,Zhang, Zhaoguo
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p. 2723 - 2730
(2016/03/05)
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- Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3
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A simple and efficient method of Friedel-Crafts acylation of arenes with succinic anhydride, phthalic anhydride and glutaric anhydride under the action of 1-butyl-3-ethylimidazolium ([bmim]Br/AlCl3 ([bmim]+) cation (ionic liquid) and ultrasound irradiation is presented. Thy purity of products was tested by GC-MS and their structures evaluated by IR and 1H NMR spectroscopy.
- Fekri, Leila Zare,Nikpassand, Mohammad
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p. 1825 - 1829
(2015/01/09)
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- Catalytic asymmetric hydrogenation of δ-ketoesters: Highly efficient approach to chiral 1,5-diols
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High turnover: An highly efficient catalytic asymmetric hydrogenation of δ-aryl-δ-ketoesters has been realized by using the chiral spiroiridium catalyst (R)-1. Chiral 1,5-diol products are obtained with excellent enantioselectivity and turnover numbers (TONs) as high as 100 000. TOF=turnover frequency. Copyright
- Yang, Xiao-Hui,Xie, Jian-Hua,Liu, Wei-Peng,Zhou, Qi-Lin
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supporting information
p. 7833 - 7836
(2013/08/23)
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- Synthesis and anti-inflammatory activity of some 3-(4,6-disubtituted-2- thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) propanoic acid derivatives
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A series of 3-(4,6-disubtituted-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) propanoic acid derivatives has been synthesized by condensation of thiourea, 5-(4-subtituted phenyl)-5-oxopentanoic acid and substituted aldehyde. The synthesized compounds were screened for their anti-inflammatory activity using rat paw edema method. Most of the compounds from the series showed significant (p 0.05) anti-inflammatory activity.
- Mokale, Santosh N.,Shinde, Sandeep S.,Elgire, Rupali D.,Sangshetti, Jaiprakash N.,Shinde, Devanand B.
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experimental part
p. 4424 - 4426
(2010/09/09)
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- Diaryl piperidines as CB1 modulators
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A compound having the general structure of Formula (I): or a pharmaceutically acceptable salt, solvate, or ester thereof, are useful in treating diseases, disorders, or conditions such as metabolic syndrome (e.g., obesity, waist circumference, lipid profile, and insulin sensitivity), neuroinflammatory disorders, cognitive disorders, psychosis, addictive behavior, gastrointestinal disorders, and cardiovascular conditions.
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Page/Page column 75-76
(2010/11/28)
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- Hypervalent iodine(III) sulfonate mediated synthesis of 5-benzoyldihydro-2(3H)-furan-one in ionic solvent
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The room temperature ionic liquid, n-butylpyridinium tetrafluoroborate(BPyBF4) is used as a "green" recyclable solvent for the reaction of 4-benzoylbutyric acid with [hydroxy-(2,4-dinitrobenzenesulfonyloxy)iodo]-benzene (HDNIB) to prepare 5-benzoyldihydro-2(3H)-furanone.
- Hou, Rei-Sheu,Wang, Huey-Min,Lin, Yu-Chien,Chen, Ling-Chieg
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p. 649 - 656
(2007/10/03)
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- 2-Aryl indole NK1 antagonists: Optimisation of the amide substituent
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The in vivo properties of a series of 2-arylindole NK1 antagonists have been improved, by modification of the amide substituent. The 1-(2-methoxyphenyl)piperazine amide was identified as a major area of metabolism in the lead compound 1. Replacement of this amine moiety by a 4-benzyl-4-hydroxypiperidine resulted in a compound 18 with reduced clearance and improved central duration of action.
- Shaw, Duncan,Chicchi, Gary G.,Elliott, Jason M.,Kurtz, Marc.,Morrison, Denise,Ridgill, Mark P.,Szeto, Nicola,Watt, Alan P.,Williams, Angela R.,Swain, Christopher J.
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p. 3031 - 3034
(2007/10/03)
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- Synthesis and pharmacological evaluation of a new series of substituted benzoyl-γ-butyrolactone derivatives
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A series of substituted benzoyl-γ-butyrolactones (1-3) has been synthesized and tested for their ability to affect central dopaminergic and GABAergic function in comparison to γ-butyrolactone (GBL).Similarly to GBL, α-, β- and γ-substituted GBLs 1-3 with one or more chlorine on the phenyl ring were found to induce central depressant effects in rats, though at different degrees.However, the test compounds modified dopamine (DA) metabolism in rat striatum differently from GBL.In fact, whereas GBL increased both DA and dihydroxyphenylacetic acid (DOPAC) content, GBL derivatives 1-3 increased DA levels, but reduced the DOPAC concentration.Moreover, some of them, unlike GBL, effectively antagonized pentylenetetrazole (PTZ)-induced seizures in mice.In particular, α-3,5-dichlorobenzoyl-GBL (1g) was effective at a dose as low a 36 mg/kg in decressing the number of animals having convulsions.However, in vitro addition and in vivo administration of the test compounds failed to modify -t-butylbicyclophosphorothionate (-TBPS) binding, which is a very sensitive tool for revealing changes in the GABAergic function. γ-butyrolactone / benzoyl-γ-butyrolactone / dopamine / anticonvulsant effect
- Cignarella, G.,Barlocco, D.,Pocar, D.,Clerici, F.,Curzu, M. M.,et al.
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p. 721 - 726
(2007/10/03)
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