17213-58-0

Usage

Chemical Properties

white to very slightly yellow powder

InChI:InChI=1/C9H11NO3/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5H,1-2H3,(H2,10,11)

Upstream product

• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 19179-31-8 3,5-dimethoxy-benzonitrile 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 75996-26-8 azido(3,5-dimethoxyphenyl)methanone 
• 51707-38-1 3,5-dimethoxy-benzoic acid hydrazide 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 
• 201230-82-2 carbon monoxide 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 
• 100-51-6 benzyl alcohol 

Downstream Products

• 5333-29-9 1-(3,5-dimethoxy-phenyl)-pentan-1-one 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 63720-48-9 1-(3,5-dimethoxyphenyl)-2-phenylethan-1-one 
• 10586-43-3 3,5-dimethoxyphenyl 1-methylhexyl ketone 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 292038-64-3 1-ethoxymethyl-3,5-dimethoxy-benzene 
• 94088-74-1 N-(3,5-dimethoxyphenyl)benzamide 
• 134029-84-8 N-(3,5-dimethoxyphenyl)-4'-methoxybenzamide 
• 72661-28-0 α-bromo-3,5-dimethoxypropiophenone 
• 67048-97-9 3-(3,5-dimethoxy-phenyl)-isothiazole-4-carboxylic acid ethyl ester 
• 67048-93-5 3-(3,5-dimethoxy-phenyl)-isothiazole-5-carboxylic acid ethyl ester 
• 904034-57-7 2-(3,5-dimethoxyphenyl)benzo[d]oxazole 
• 331828-12-7 N-benzyl-3,5-dimethoxybenzamide 

Relevant academic research and scientific papers

Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides

A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

Base-Mediated Amination of Alcohols Using Amidines

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.

Synthesis method of resveratrol

The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.

Palladium on manganese ferrite: An efficient catalyst for one pot synthesis of primary amides from iodobenzene

Amidation of aryl iodide in one pot is reported using Pd-MnFe2O4 as a catalyst. The catalyst was characterized by various techniques such as XRD, FEG-SEM, EDS, TEM, BET surface area and ICP AES. K4[Fe(CN)6]is used as a non toxic cyanation reagent for in situ generation of benzonitrile and hydrolyzed as soon as it formed. The catalyst was found to be efficient and can be used for several cycles without loss in activity. Good to excellent yields of primary amides were obtained.

Sequential one-pot synthesis of benzoxazoles from aryl bromides: Successive palladium- and copper-catalyzed reactions

A convenient one-pot process has been developed for the synthesis of benzoxazoles. Starting from aryl bromides and 1,2-dibromobenzenes palladium-catalyzed aminocarbonylation and subsequent copper-catalyzed coupling reaction gave a variety of substituted benzoxazoles in moderate to good yields.

Synthesis and antibacterial activities of pleuromutilin derivatives with thiazole-5-carboxamide and thioether moiety

Seven novel pleuromutilin derivatives with thiazole-5-carboxamide and thioether moiety in the C14 side chain were designed and synthesised. The antibacterial activities of the target compounds were tested via agar-well diffusion method in vitro. The results showed that three target compounds still had antibacterial activity against Staphylococcus aureus ATCC26112 and Staphylococcus aureus SC at a low concentration of 0.05 μg mL-1.

Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain

We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.

Substituted benzamide radiosensitizers

A method for sensitizing hypoxic tumor cells to radiation using derivatives of benzamide are disclosed. Some of the compounds useful in the REFERENCE TO GOVERNMENT GRANT OR CONTRACT The invention described herein was made in the course of work under grant or contract from the National Institutes of Health.

FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE

Sodium perborate in acetic acid is an effective reagent for the oxidation of aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes, azines to N-oxides, and various types of sulfur heterocycles to S,S-dioxides.Nitriles are unaffected by the reagent in acetic acid, but undergo smooth hydration to amides when aqueous methanol is employed as solvent.