33524-31-1

Usage

Uses

Used in Chemical Synthesis:
2,5-Dimethoxybenzyl alcohol is used as a starting reagent for the synthesis of various organic compounds. It serves as a key component in the production of [(S)S]-3,6-dimethoxy-2-(p-tolylsulfinyl)-benzaldehyde, daunornycinone, and pillar[n]arenes (n = 5 or 6) via cyclooligomerization reaction with an appropriate Lewis acid catalyst.
Used in Analytical Chemistry:
2,5-Dimethoxybenzyl alcohol is used as a self-indicating standard for the determination of organolithium reagents. Its properties make it a valuable tool in the analysis and quantification of these reagents, contributing to the accuracy and reliability of chemical measurements in research and industry.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6207, 1994 DOI: 10.1016/S0040-4039(00)73392-2

InChI:InChI=1/C9H12O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-5,10H,6H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 495-08-9 gentisyl alcohol 
• 67698-75-3 2,5-dimethoxybenzyl acetate 
• 150-78-7 1,4-dimethoxybezene 
• 138250-68-7 2,5-dimethoxybenzyl benzoate 
• 159184-68-6 1,4-dimethoxy-2-(pivaloyloxomethyl)benzene 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 33593-01-0 2-(3,6-Dimethoxy-2-methyl-phenyl)-N,N-dimethyl-acetamide 
• 120475-83-4 2-(hydroxymethyl)-1,4-dimethoxybenzene hydrogen succinate 
• 130716-99-3 4-(2-cyano-2-methylethyl)-2,5-dimethoxybenzyl alcohol 
• 101537-09-1 1,15-bis(2,5-dimethoxyphenyl)-2,5,8,11,14-pentaoxapentadecane 
• 71255-03-3 2,5-dimethoxybenzyl vinyl ether 
• 103441-37-8 1,4-dimethoxy-2-methoxymethyl-benzene 
• 630108-35-9 2-[(2,5-dimethoxyphenyl)methoxy]-1H-isoindole-1,3(2H)-dione 
• 601519-39-5 [3,6-Dimethoxy-2-((S)-toluene-4-sulfinyl)-phenyl]-methanol 
• 644-17-7 2-hydroxymethyl-1,4-benzoquinone 
• 138250-68-7 2,5-dimethoxybenzyl benzoate 
• 159184-68-6 1,4-dimethoxy-2-(pivaloyloxomethyl)benzene 

Relevant academic research and scientific papers

1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach

The preparation of various 1-trifluoromethylisoquinolines from α-benzylated tosylmethyl isocyanide derivatives and the commercial Togni reagent using a radical cascade is reported. The starting isocyanides are readily prepared in a modular sequence from commercial tosylmethyl isocyanide via sequential double α-alkylation, and the radical reaction proceeds under mild conditions with high efficiency without any transition-metal catalyst via electron catalysis. This valuable protocol has been successfully applied to the total synthesis of CF3-mansouramycin B.

Selective Deprotection of Esters Using Magnesium and Methanol

The use of magnesium metal in methanol for the deprotection of alkyl esters is described.This mild reagent also provides good to excellent selectivity to cleave different esters.The order of reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate > acetate > benzoate > pivaliate >> trifluoroacetamide.

Synthesis of new iron-NHC complexes as catalysts for hydrosilylation reactions

A series of new piano-stool iron(II) complexes comprising N-heterocyclic carbene ligands [Fe(Cp)(CO)2(NHC)]I (NHC = 1,3-disubstituted imidazolidin-2-ylidene) have been synthesized and analyzed by 1H NMR, 13C NMR, IR, elemental analysis and mass spectrometric techniques. These compounds were easily prepared from the reaction of disubstituted imidazolidin-2-ylidene with [FeI(Cp)(CO)2] in toluene at room temperature. These complexes were tested in the catalytic hydrosilylation reaction of aldehydes and ketones with phenylsilane in solvent-free conditions. After a basic hydrolysis step, the corresponding alcohols were obtained in good yields. Copyright

Selective deprotection of alkyl esters using magnesium methoxide

The use of magnesium methoxide for the deprotection of alkyl esters is described. This mild reagent provides a good method to cleave esters efficiently and more importantly, allows for effective differentiation between two different esters. The order of the reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate > acetate > benzoate > pivaloate >> acetamide.

Preparation method of 2,5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2,5-dimethoxyphenylacetic acid, wherein the method comprises the following steps: A,reacting 1,4-dimethoxybenzene in a formylation system to obtain 2,5-dimethoxybenzaldehyde; B, reacting the 2,5-dimethoxybenzaldehyde obtained in the step A with a reducing agent, extracting a reaction system, then combining organic phases, drying, concentrating under reduced pressure and distilling a crude product to obtain 2,5-dimethoxybenzyl alcohol; C, reacting the 2,5-dimethoxybenzyl alcoholobtained in the step B with a bromination reagent to obtain 2-bromomethyl-1,4-dimethoxybenzene; and D, reacting the 2-bromomethyl-1,4-dimethoxybenzene obtained in the step C with magnesium or butyl lithium and carbon dioxide in a solvent to obtain the 2,5-dimethoxyphenylacetic acid. The yield and the total yield of the 2,5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of 2,5-dimethoxyphenylacetic acid synthesized by a Willegerdt-Kindler method.

Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor

The sphingomyelin synthase 2 (SMS2) is a potential target for pharmacological intervention in atherosclerosis. However, so far, few selective SMS2 inhibitors and their pharmacological activities were reported. In this study, a class of 2-benzyloxybenzamides were discovered as novel SMS2 inhibitors through scaffold hopping and structural optimization. Among them, Ly93 as one of the most potent inhibitors exhibited IC50 values of 91 nM and 133.9 μM against purified SMS2 and SMS1 respectively. The selectivity ratio of Ly93 was more than 1400-fold for purified SMS2 over SMS1. The in vitro studies indicated that Ly93 not only dose-dependently diminished apoB secretion from Huh7 cells, but also significantly reduced the SMS activity and increased cholesterol efflux from macrophages. Meanwhile, Ly93 inhibited the secretion of LPS-mediated pro-inflammatory cytokine and chemokine in macrophages. The pharmacokinetic profiles of Ly93 performed on C57BL/6J mice demonstrated that Ly93 was orally efficacious. As a potent selective SMS2 inhibitor, Ly93 significantly decreased the plasma SM levels of C57BL/6J mice. Furthermore, Ly93 was capable of dose-dependently attenuating the atherosclerotic lesions in the root and the entire aorta as well as macrophage content in lesions, in apolipoprotein E gene knockout mice treated with Ly93. In conclusion, we discovered a novel selective SMS2 inhibitor Ly93 and demonstrated its anti-atherosclerotic activities in vivo. The preliminary molecular mechanism-of-action studies revealed its function in lipid homeostasis and inflammation process, which indicated that the selective inhibition of SMS2 would be a promising treatment for atherosclerosis.

CD16A BINDING AGENTS AND USES THEREOF

Among other things, the present disclosure provides compounds, compositions thereof, and methods of using the same. In some embodiments, compounds of the present disclosure bind to Fc receptors, e.g., CD16a. In some embodiments, compounds of the present disclosure are useful for treating various conditions, disorders or diseases including cancer.

3, 5-disubstituted hydantoin compound as well as preparation method and application thereof

The invention provides a 3, 5-disubstituted hydantoin compound as well as a preparation method and an application thereof. The structure of the compound is shown in formula I in the description. The application of the 3, 5-disubstituted hydantoin compound shown in the formula I or solvates, hydrates or salts of the compound in preparation of medicines for treating Alzheimer's disease, vascular dementia and other dementia diseases with memory impairment also belongs to the protection scope. Animal experiments prove that the compound has the effect of saving memory of animal models, has high safety, does not have mutagenicity, can stay in blood for several hours after oral administration and intravenous injection, and can enter the brain.

IRIDIUM-BASED CATALYSTS FOR HIGHLY EFFICIENT DEHYDROGENATION AND HYDROGENATION REACTIONS IN AQUEOUS SOLUTION AND APPLICATIONS THEREOF

A series of iridium-based catalysts for dehydrogenation of formic acid, and hydrogenation using formic acid as the hydrogen source, and the process using the catalyst(s) to produce hydrogen gas from formic acid solution, or to reduce aldehydes using formic acid, are disclosed and claimed. More specifically, the present invention relates to a group of pentamethylcyclopentadienyl (Cp*) iridium complexes with different Ν,Ν-bidentate ligands that catalyze dehydrogenation from formic acid, and chemo-selective hydrogenation of aldehydes, in the aqueous solution system in a highly efficient, and long life-time manner.

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

A water-soluble highly efficient iridium catalyst is developed for the chemoselective reduction of aldehydes to alcohols in water. The reduction uses formic acid as the traceless reducing agent and water as a solvent. It can be carried out in air without the need for inert atmosphere protection. The products can be purified by simple extraction without any column chromatography. The catalyst loading can be as low as 0.005 mol% and the turn-over frequency (TOF) is as high as 73 800 mol mol-1 h-1. A wide variety of functional groups, such as electron-rich or deficient (hetero)arenes and alkenes, alkyloxy groups, halogens, phenols, ketones, esters, carboxylic acids, cyano, and nitro groups, are all well tolerated, indicating excellent chemoselectivity.