533-31-3Relevant articles and documents
Design and synthesis of 3,4-methylenedioxy-6-nitrophenoxyacetylhydrazone derivatives obtained from natural safrole: New lead-agents with analgesic and antipyretic properties
Bezerra-Netto, Heleno J.C.,Lacerda, Daniel I.,Miranda, Ana Luisa P.,Alves, Helio M.,Barreiro, Eliezer J.,Fraga, Carlos A.M.
, p. 7924 - 7935 (2006)
In this work, we reported the synthesis and evaluation of the analgesic, anti-inflammatory, and antipyretic properties of new 2-(6-nitro-benzo[1,3]dioxol-5-yloxy)-acetylhydrazone derivatives (3), designed exploring molecular hybridization and isosteric replacement approaches between nimesulide (1) and carbanalogue NAH series (2) developed at LASSBio. Target compounds were synthesized in very good yields exploiting abundant Brazilian natural product safrole (4) as starting material. The evaluation of the antinociceptive properties of this series led us to discover a new potent prototype of analgesic and antipyretic agent, that is, NAH derivative 3c, named LASSBio-891, which showed to be more potent than dipyrone used as standard.
Formation of Samin Diastereomers by Acid-Catalyzed Transformation of Sesamolin with Hydrogen Peroxide
Chu, I-Hsuan,Hung, Wei-Ching,Lee, Wei-Ju,Su, Nan-Wei,Tsai, Hsin-Ya
, p. 6430 - 6438 (2020)
The conversion of sesame lignans is of interest because the derived products may have potential applications. Here, in investigating the transformation of sesamin and sesamolin, main endogenous sesame lignans in sesame seeds, in both acidic aqueous and anhydrous systems, 7R,7′S-samin was identified as one of the major products of sesamolin in both systems catalyzed with common inorganic acids, but sesaminol was not generated. In investigating the effect of different oxidizing agents on the acid-catalyzed conversion of sesame lignans, 7R,7′S-samin was still the major product of sesamolin, whereas sesamolin as well as 7R,7′S-samin stereoselectively rendered 7R,7′R-samin in the presence of hydrogen peroxide. Hydrogen peroxide may play a role in stabilizing the transitional oxonium ions, derived from acid hydrolysis of sesamolin or 7R,7′S-samin by forming a seven-membered ring intermediate through hydrogen bonding, to consequently produce 7R,7′R-samin as the final product.
Synthesis process 3,4 -methylenedioxy phenol
-
Paragraph 0027; 0031; 0033; 0037; 0038; 0042; 0043; ..., (2021/10/30)
The invention relates to the technical field of compound synthesis, in particular to a synthesis process of 3,4 -methylenedioxy phenol, which comprises the following steps: 3,4 - methylenedioxy acetophenone. The second Catalyst, first solvent was added to the autoclave, and an oxidant was added, and reacted 25 - 50 °C under 4 - 8h, and the first solvent was separated and the solvent was separated. The resulting 3,4 -methylenedioxy phenol acetate is obtained. The second Solvent, sodium hydroxide solution was added to the autoclave, and reacted 20 - 60 °C at 2 - 6h, adjusted pH to 3-6 to obtain 3,4 - methylenedioxy phenol. The method solves the problems that 3,4 -methylenedioxy acetophenone in the prior art is low in yield and large in separation difficulty in preparation of sesame phenol. The process takes the pepper ring as the starting raw material and is divided into three-step reaction synthesis, the raw material conversion rate is high, no other side reaction is avoided, the reaction condition is mild, the production cost is low, and the product quality is better.
AN EFFICIENT PROCESS FOR PREPARATION OF ACYL DERIVATIVES OF ALKYLENEDIOXYBENZENES
-
, (2021/08/20)
The present disclosure provides a process of preparation of compounds of Formula I comprising the step of : reacting an alkylenedioxybenzene compound of Formula II with an acyl halide of Formula III in presence of a solvent, wherein the step of reacting the alkylenedioxybenzene compound of Formula II with the acyl halide of Formula III is effected in presence of an amphoteric oxide and a Lewis acid so as to immediately quench the compound of formula H-X, formed during the course of the reaction, to substantially eliminate degradation of the compound of any of Formula I and II. The present disclosure also provides for process(es) for preparation of compound of Formula IVa, IVb and IVc.
Preparation method of sesamol
-
Paragraph 0022; 0026; 0032-0035, (2021/11/21)
The invention belongs to the technical field of compound synthesis, and particularly relates to a preparation method of sesamol, which firstly prepares 2 -chloro -1, 4 -diphenol, and then 2 - chlorine -1, 4 -biphenol and sodium hydroxide in an aqueous solution to obtain the sesamol, namely 1 2, 1 2 4 - 4 -triphenol and dichloromethane. The invention provides a new method for preparing the sesame phenol, and the yield of the sesamol is remarkably improved.
Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
supporting information, (2021/09/28)
An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.
Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst
-
Paragraph 0025-0028; 0030-0032, (2020/01/25)
The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.
Development of a Cross-Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)-ABX
Huang, Jing-Kai,Shia, Kak-Shan
supporting information, p. 6540 - 6545 (2020/03/03)
The cross-conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael-type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7-step sequence with an overall yield of about 20 %.
Rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids under sunlight: DFT mechanistic studies
Golla, Sivaparwathi,Poshala, Soumya,Pawar, Ravinder,Kokatla, Hari Prasad
supporting information, (2019/12/27)
A novel rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids has been developed. This method employs low-cost rongalite as a radical initiator and O2 as a green oxidizing agent for ipso-hydroxylation. This protocol is compatible with a wide variety of functional groups with good to excellent yields at room temperature. Furthermore, mechanistic insight into the role of superoxide radical anions in C-B cleavage has also been provided based on DFT studies.
Bimetallic photoredox catalysis: Visible light-promoted aerobic hydroxylation of arylboronic acids with a dirhodium(ii) catalyst
Campbell, Michael G.,Chuang, Gary Jing,Liu, Ming-Lun,Miura-Stempel, Emily,Tu, Jing-Wen,Yang, Hsiang-Ming
, p. 2040 - 2047 (2020/03/13)
We report the use of a rhodium(II) dimer in visible light photoredox catalysis for the aerobic oxidation of arylboronic acids to phenols under mild conditions. Spectroscopic and computational studies indicate that the catalyst Rh2(bpy)2(OAc)4 (1) undergoes metal-metal to ligand charge transfer upon visible light irradiation, which is responsible for catalytic activity. Further reactivity studies demonstrate that 1 is a general photoredox catalyst for diverse oxidation reactions.
