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Studies on the chemical constituents of xanthoxylum nitidum (ROXB.) D.-C. (Fagara nitida ROXB.). III. The chemical constituents of the wood

the chemical constituents of the wood of Xanthoxylum nitidum (roxb.) D. C. (Fagara nitida ROXB.) were examined. Two phenylpropanoids, methyl nitinoate (2) and dihydrocuspidiol (3), and a benzodioxane type lignan, nitidanin (4), were newly isolated. The structures of the phenylpropanoids were chemically determined. In addition, the application of a selective insensitive nuclei enhanced by polarization transfer selective (INEPT) technique in the NMR spectrum to the new lignan allowed us to deduce the structure.

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Convenient Synthesis of Disubstituted Cyclic Ethers. Syntheses of (-)-cis-Rose Oxide and (cis-6-Methyltetrahydropyran-2-yl)acetic Acid

Disubstituted cyclic ethers are stereoselectively prepared on the successive treatment of delta- or epsilon-lactones with t-butyldimethylsiloxy-1-ethoxyethene and silyl nucleophiles in the presence of a catalytic amount of trityl hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II) iodide.The present procedure is effectively applied to short syntheses of (-)-cis-rose oxide and (cis-6-methyltetrahydropyran-2-yl)acetic acid, a constituent of civet.

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DIURETICS

A compound having the structure (I) wherein R is selected from the group consisting of 1) and 2), or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.

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From olefins to alcohols: Efficient and regioselective ruthenium-catalyzed domino hydroformylation/reduction sequence

Exploring the alternatives: Ruthenium imidazoyl phosphine complexes catalyze the domino hydroformylation/reduction of alkenes to alcohols in good yields and with good selectivities (see scheme). Linear aliphatic alcohols are synthesized under reaction conditions typically used in industrial hydroformylations. Copyright

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1679-47-6, 3-Methyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2 wt. % MGBL in 60 mL H2O, 1.0 g 5 wt. % Ru/C, 140 bar. Data reported at time of maximum MBDO selectivity: 80 C. (71 h-did not reach maximum), 100 C. (6.3 h), 120 C. (3.5 h), 140 C. (1.8 h), 160 C. (0.3 h), 200 C. (0.3 h). Pd/C (1.5 h), Pt/C (1.5 h).

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Reference£º
Patent; REGENTS OF THE UNIVERSITY OF MINNESOTA; Dauenhauer, Paul J.; Spanjers, Charles; Zhang, Kechun; (37 pag.)US2017/297983; (2017); A1;,
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Step 1: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2*). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta7.53 (d, J=8.6 Hz, 1H), 6.97 (d, J=2.4 Hz, 1H), 6.85 (dd, J=8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (EI) m/z 241.16 (M+-H). 1679-47-6, As the paragraph descriping shows that 1679-47-6 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2007/224636; (2007); A1;,
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To a solution of diisopropylamine (2.3 mL, 16.16 mmol) in tetrahydrofuran (THF) (37 mL),N-Butyllithium (2.5 M in hexanes, 5.92 mL, 14.81 mmol) was added with stirring at -78 C. After stirring for 5 minutes,Alpha-methyl-gamma-butyrolactone(1.416 mL, 14.81 mmol) was added dropwise.After stirring at 0 C for 15 minutes,The reaction mixture is cooled to -75 C.2,6-Dichloropyrazine (2.0059 g, 13.46 mmol) was added dropwise as a solution in THF (7.5 mL). The mixture was stirred overnight while warming to room temperature.Dilute the reaction mixture with saturated aqueous sodium bicarbonate solution,Extracted with dichloromethane (2 ¡Á 10 mL).The combined extracts are dehydrated with anhydrous sodium sulfate,Filter and concentrate under reduced pressure. ProductPurify by silica gel chromatography eluting with 0-40% ethyl acetate / heptane,The desired product (2.5 g, 76% yield) was obtained.

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Reference£º
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
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General procedure: IA hydrogenation reactions were conducted in a 50 mL stain-less steel autoclave with magnetic stirring. In every experiment,0.2 g IA, 0.1 g catalyst and 20 mL deionized water were placed inthe autoclave. Afterwards, the autoclave was purged with hydro-gen for five times to remove air and pressured up to the desiredhydrogen pressure and then heated to the reaction temperature., 1679-47-6

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Reference£º
Article; Liu, Xiaoran; Wang, Xicheng; Liu, Qiang; Xu, Guoqiang; Li, Xuemin; Mu, Xindong; Catalysis Today; vol. 274; (2016); p. 88 – 93;,
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Typical Procedure: Palladium acetate (45 mg, 0.2 mmol, 0.1 eq.) and R-(+)-BINAP (156 mg, 0.25 mmol, 0.125 eq.) in dry toluene (30 mL, degased with dry nitrogen) were stirred at room temperature under nitrogen for 60 minutes. Aryl bromide (4 mmol, 2.0 eq.) and alpha-methyl-gamma-butyrolactone (2 mmol) were added via syringe. KN(TMS)2 in toluene (0.5 M, 7 mL, 3.5 mmol, 1.75 eq.) was added dropwise and the resultant dark red solution was then stirred at 100-105 C. for 24 hours. The reaction mixture was cooled to room temperature before treating with 1N HCl (15 mL) and water (50 mL). The mixture was extracted with ethyl acetate (3¡Á50 mL) and the combined organic phase was washed with water (25 mL) and brine (40 mL) and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica gel (heptane: ethyl acetate=8:1?2:1) to afford the product., 1679-47-6

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Reference£º
Patent; Zhang, Tony Yantao; Zhang, Hongbin; Proctor, Christophor Scott; US2003/225282; (2003); A1;,
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Synthesis of (¡À)-2-methyl-4-bromobutyric acid (II) Under nitrogen protection, (¡À)-alpha-methyl-gamma-butyrolactone (I) (7.33 g, 73.3 mmol) was transferred to a reaction flask in ice water. Under a bath condition, slowly add 33% HBr acetic acid solution (51.3 mL, 147 mmol, 2.0 eq.) to the reaction flask. After stirring for 6 hours at room temperature, TLC monitoring showed that the conversion of the starting material I was completed, stirring was stopped, and the reaction solution was placed in a fume hood. After pouring into 250 mL of CH2Cl2 cooled in an ice water bath, a large amount of white smoke emerged and the resulting solution was successively treated with water (50 mL x 2). After washing with saturated NaHSO 3 solution (100 mL¡Á2) and saturated brine (50 mL), the solid was dried over anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to give 12.5 g of pale yellow oil II (yield 94.2%). The product was not purified. Can be used for the next reaction., 1679-47-6

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Reference£º
Patent; Zhejiang Pharmaceutical Co., Ltd. Xinchang Pharmaceutical Factory; Ji Li; Lao Xuejun; Jin Xin; Shen Dadong; Wu Guofeng; (11 pag.)CN107488176; (2017); A;,
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