7498-88-6Relevant academic research and scientific papers
Highly selective production of propionic acid from lactic acid catalyzed by NaI
Feng, Huan,Li, Teng,Liu, Shengqin,Rong, Nianxin,Wang, Yantao,Yang, Weiran
, p. 7468 - 7475 (2020/11/23)
Propionic acid (PA), a valuable chemical widely used in the food and feed industry, is currently produced by the petrochemical industry. Selective production of PA from bio-based lactic acid (LA) is difficult due to the high activation energy of the hydroxyl group at the α position of the carboxyl group. Herein, a metal-free catalytic system for the highly selective transformation of bio-based LA to PA, which was used as the solvent to simplify the separation step, is reported using NaI as the catalyst. Under the optimal reaction conditions, a >99% yield of PA can be obtained from LA. A heat-induced radical-activated hydrogen mechanism was proposed based on the kinetic study and intermediate capture. The metal-free system can be reused five times without any loss in activity, and the PA product is easily separated. In addition, a two-step method using cellulose as the raw material to produce PA was conducted. This strategy offers a green and efficient approach to synthesize PA from biomass resources. This journal is
Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid
Fu, Ming-Chen,Shang, Rui,Cheng, Wan-Min,Fu, Yao
, p. 8818 - 8822 (2017/07/11)
Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.
Method for preparing beta, gama-unsaturated carboxylic acid compound
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Paragraph 0041; 0042; 0043; 0044; 0045; 0046; 0047-0083, (2017/12/04)
The invention provides a method for preparing a beta, gamma-unsaturated carboxylic acid compound. The method comprises the steps of making an allylic alcohol compound of a formula 1 or a formula 2 react with formic acid in the presence of a palladium catalyst, a phosphorous ligand, acid anhydride and an organic solvent to obtain the beta, gamma-unsaturated carboxylic acid compound of a formula 3 or formula 4, wherein R1, R2 and R3 are defined in the description. Formic acid is utilized as a carboxylation reagent, and the beta, gamma-unsaturated carboxylic acid compound is low in price, safe, stable and low in toxicity; the yield is high, the operation is simple, and the economy is high; compared with an existing compounding method, the use of toxic gas carbon monoxide and/or an equivalent quantity of reactive metal reagents is avoided, and the method meets requirements for environment-friendly chemistry; in addition, the dose of catalysts is small, the reaction condition is mild, the reactant is high in conversion rate and product yield, and the method has a very good industrial prospect.
Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide
Moragas, Toni,Martin, Ruben
, p. 2816 - 2822 (2016/08/26)
A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.
Palladium-Catalyzed ?±-Arylation of Aryl Acetic Acid Derivatives via Dienolate Intermediates with Aryl Chlorides and Bromides
Sha, Sheng-Chun,Zhang, Jiadi,Walsh, Patrick J.
supporting information, p. 410 - 413 (2015/03/04)
To date, examples of ?±-arylation of carboxylic acids remain scarce. Using a deprotonative cross-coupling process (DCCP), a method for palladium-catalyzed ?3-arylation of aryl acetic acids with aryl halides has been developed. This protocol is applicable to a wide range of aryl bromides and chlorides. A procedure for the palladium-catalyzed ?±-arylation of styryl acetic acids is also described.
Inhibition of activated STAT5 in Bcr/Abl expressing leukemia cells with new pimozide derivatives
Rondanin, Riccardo,Simoni, Daniele,Romagnoli, Romeo,Baruchello, Riccardo,Marchetti, Paolo,Costantini, Cristiana,Fochi, Sara,Padroni, Giacomo,Grimaudo, Stefania,Pipitone, Rosaria Maria,Meli, Maria,Tolomeo, Manlio
supporting information, p. 4568 - 4574 (2015/02/19)
STATs are transcription factors acting as intracellular signaling after stimulation with cytokines, growth factors and hormones. STAT5 is also constitutively active in many forms of cancers, including chronic myelogenous leukemia, acute lymphoblastic leukemia and Hodgkin's lymphoma. Recently, literature reported that the neuroleptic drug pimozide inhibits STAT5 phosphorylation inducing apoptosis in CML cells. We undertook an investigation from pimozide structure, obtaining simple derivatives with cytotoxic and STAT5-inhibitory activity, two of them markedly more potent than pimozide.
An approach to enantioselective 5-endo halo-lactonization reactions
Garnier, Jean Marc,Robin, Sylvie,Rousseau, Gerard
, p. 3281 - 3291 (2008/02/10)
Enantioselective lactonization of 4-substituted but-3-enoic acids using iodobis(N-methylephedrine) hexafluoroantimonate in dichloromethane at low temperatures is reported. The presence of bis(N-methylephedrine)silver(I) hexafluoroantimonate, derived from
Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
Hudgens, Debjani P.,Taylor, Catherine,Batts, Timothy W.,Patel, Manoj K.,Brown, Milton L.
, p. 8366 - 8378 (2008/02/05)
The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [3H]-BTX binding site and sodium currents of hNav1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Nav1.2 currents at 10 μM, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNav1.2 activity and modification of the amine portion is detrimental to sodium channel block.
A new synthesis of β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic acid chlorides and α,β-alkenyl aldehydes with one-carbon elongation
Satoh, Tsuyoshi,Nakamura, Akira,Iriuchijima, Atsuko,Hayashi, Yasumasa,Kubota, Ko-Ichi
, p. 9689 - 9696 (2007/10/03)
Reaction of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide with α,β-alkenyl carboxylic acid chlorides gave γ,δ-alkenyl α-chloro-β-keto sulfoxides in variable yields. The keto sulfoxides were also synthesized from α,β-alkenyl aldehydes in two steps in good overall yields: addition of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide to α,β-alkenyl aldehydes followed by oxidation of the adducts with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or Dess-Martin periodinane. These products were treated in sequence with potassium hydride, tert-butyllithium, and 5% aqueous sodium hydroxide, in one flask to give β,γ-alkenyl carboxylic acids with one-carbon elongation in good yields. The procedure offers a new method for synthesizing β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic acid chlorides and α,β-alkenyl aldehydes with one-carbon elongation.
Stereoseleetive Syntheses of β,γ-Unsaturated Esters and γ-Lactones: 1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected =CCH2CO2Et Synthon Equivalent
Katritzky, Alan R.,Feng, Daming,Lang, Hengyuan
, p. 4131 - 4136 (2007/10/03)
l-(Benzotriazol-l-yl)-3-(diphenylphosphoryl)-l-ethoxy-l-propene (3), prepared from N-(α-ethoxyallyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced β,γ-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding γ,γ-disubstituted β,γ-unsaturated esters 11a-d or γ-lactones 9a-c and 13. A double lithiation process provided β,γ,γ-trisubstituted β,γ-unsaturated esters 15, 18, and β,γ,γ-trisubstituted γ-lactone 14.
