15484-46-5Relevant articles and documents
A unique heterogeneous nucleophilic catalyst comprising methylated nitrogen-substituted porous silica provides high product selectivity for the Morita-Baylis-Hillman reaction
Furukawa, Yutaro,Ogura, Masaru
, p. 119 - 121 (2014)
Methylated nitrogen-substituted microporous and mesoporous silica exhibited almost the same catalytic performance as that of a conventional homogeneous base catalyst. They also demonstrated unexpectedly high product selectivity for the Morita-Baylis-Hillman reaction of formaldehyde with methyl acrylate at high temperatures.
New insights into the alkoxycarbonylation of propargyl alcohol
Scrivanti,Beghetto,Bertoldini
, p. 38 - 42 (2017)
The challenging carbonylation of propargyl alcohol is effectively catalyzed by Pd(OAc)2 in combination with diphenyl-(6-methyl-pyridin-2-yl)phosphine and methanesulfonic acid. In dichloroethane at 20–50 °C, the reaction affords with almost complete regioselectivity alkyl 2-(hydroxymethyl)acrylates. Turnover frequency numbers (TOF) of up to 450 h?1 can be achieved working at 50 °C, while a maximum turnover number (TON) of about 730 is obtained at 30 °C. The catalyst longevity is limited because the carbonylation product reacts with the phosphorus atom of the ligand to give a quaternary phosphonium salt. This reaction leads to deactivation of the catalyst and eventually to palladium black formation.
Synthesis of cynaropicrin-d4
Sato, Takuya,Hara, Shihori,Sato, Makiko,Ogawa, Keita,Adams, Michael,Usuki, Toyonobu
, p. 5504 - 5507 (2015)
Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead.
Stereoselective synthesis of the (?)-dysiherbaine furopyran core via BF3-promoted formal [3+2] annulation of aldehydo-aldoses with allylsilanes
Hotoda, Koki,Ohnuma, Asami,Kusakabe, Kosuke,Tanaka, Aki,Sasaki, Ikuo,Sugimura, Hideyuki
, p. 5359 - 5362 (2016)
A highly stereoselective synthesis of the hexahydrofuro[3,2-b]pyran core of (?)-dysiherbaine is described. The key step in this synthesis includes the stereocontrolled formation of the tetrahydrofuran ring using the formal [3+2] annulation of the isopropylidene-protected aldehydo-L-arabinose and the β-substituted allylsilane mediated by trifluoroborane etherate.
Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols
Meng, Ling,Chang, Xiaoyong,Lin, Zhenyang,Wang, Jun (Joelle)
supporting information, p. 2663 - 2667 (2021/04/07)
A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
supporting information, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Phosphine-Catalyzed Cascade Annulation of MBH Carbonates and Diazenes: Synthesis of Hexahydrocyclopenta[c]pyrazole Derivatives
Guo, Hongchao,Li, Hongxiang,Liu, Hao,Shi, Wangyu,Wang, Chang,Wang, Wei,Wu, Yongjun
supporting information, p. 5571 - 5575 (2021/07/31)
A phosphine-catalyzed cascade annulation of Morita-Baylis-Hillman (MBH) carbonates and diazenes was achieved, giving tetrahydropyrazole-fused heterocycles bearing two five-membered rings in moderate to excellent yields. The reaction underwent an unprecedented reaction mode of MBH carbonates, in which two molecules of MBH carbonates were fully merged into the ring system.
Reaction type ultraviolet light absorber and preparation method and application thereof
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Paragraph 0047-0049, (2020/07/03)
The invention discloses a reaction type ultraviolet light absorber as well as a preparation method and application thereof. The method is characterized by comprising the following steps; with paraformaldehyde as an initial raw material, synthesizing 2-(bromomethyl) methyl acrylate; then carrying out a reaction on the 2-(bromomethyl) methyl acrylate and 2,2',4,4'-dichlorophenol as a reactant by controlling the temperature, and the types of the solvents and alkalis to obtain the reaction type ultraviolet light absorber. The reaction type ultraviolet light absorber contains unsaturated carbon-carbon double bonds, wherein the main ultraviolet light absorption range is 250-400 nm; the reaction type ultraviolet light absorber is a novel broad-spectrum ultraviolet light absorber, the synthesis process is convenient to operate, the raw materials are low in price and easy to obtain, and the reaction type ultraviolet light absorber has very high market value and application value.
HYDROXYL GROUP-CONTAINING VINYL COMPOUND PRODUCTION PROCESS
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Paragraph 0051-0055, (2020/06/30)
PROBLEM TO BE SOLVED: To provide a hydroxyl group-containing vinyl compound production process in which a hydroxyl group-containing vinyl compound, in which the content of ether dimer of hydroxyl group-containing vinyl compound having high skin irritancy is sufficiently suppressed, can be produced at a lower cost than before. SOLUTION: Provided is a hydroxyl group-containing vinyl compound production process. The production process comprises a step of reacting an acrylic acid ester and an aldehyde compound in the presence of a tertiary amine compound, and a step of removing the acrylic acid ester from the reaction liquid after the reaction step, and is characterized in that the content of the ether dimer of the hydroxyl group-containing vinyl compound in the reaction liquid after the acrylic acid ester removing step is 9.0 mass% or less with respect to 100 mass% of the hydroxyl group-containing vinyl compound. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source
Correia, José Tiago Menezes,Piva da Silva, Gustavo,André, Elias,Paix?o, Márcio Weber
supporting information, p. 5558 - 5564 (2019/09/16)
No Abstract. (Figure presented.).
