838-96-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxyphenylacetonitrile is used as a key intermediate in the synthesis of Desmethylvenlafaxine, an antidepressant medication. It contributes to the production of this medication by facilitating the formation of its active components, thereby aiding in the treatment of depression and related mood disorders.
Additionally, 4-Benzyloxyphenylacetonitrile is used as an intermediate in the preparation of RAGE antagonists. These antagonists are essential in the development of treatments for Alzheimer's disease, as they target and modulate the Receptor for Advanced Glycation End-products (RAGE). This interaction helps in managing the progression of neurodegenerative symptoms associated with Alzheimer's, offering potential therapeutic benefits for patients suffering from this condition.

InChI:InChI=1/C15H13NO/c16-11-10-13-6-8-15(9-7-13)17-12-14-4-2-1-3-5-14/h1-9H,10,12H2

Upstream product

• 14191-95-8 4-cyanomethylphenol 
• 100-44-7 benzyl chloride 
• 143-33-9 sodium cyanide 
• 836-42-0 4-benzyloxybenzyl chloride 
• 100-39-0 benzyl bromide 
• 13435-20-6 tetraethylammoniumcyanide 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 392717-83-8 1-(benzyloxy)-4-((methoxymethoxy)methyl) benzene 
• 151224-18-9 C₁₅H₁₅O₅S^(1-)*Na⁽¹⁺⁾ 
• 773837-37-9 sodium cyanide 
• 5544-60-5 4-(benzyloxy)benzyl bromide 
• 1432484-52-0 1-(benzyloxy)-4-(2,2-difluorovinyl)benzene 
• 16652-64-5 O-benzyl-S-tyrosine 

Downstream Products

• 84199-13-3 4-benzyloxybenzene-acetamide 
• 139346-94-4 2-(4-Benzyloxy-phenyl)-N-hydroxy-acetamidine 
• 141805-72-3 2-(4-Benzyloxy-phenyl)-acetimidic acid ethyl ester; hydrochloride 
• 14191-95-8 4-cyanomethylphenol 
• 167762-83-6 2-(4-benzyloxyphenyl)-2-methylpropanenitrile 
• 51179-05-6 2-(4-(benzyloxy)phenyl)ethanamine 
• 1260767-69-8 1-(4-(benzyloxy)phenyl)cyclopropanecarbonitrile 

Relevant academic research and scientific papers

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

TETRAHYDROPROTOBERBERINE COMPOUND, PREPARATION METHOD THEREFOR AND USES THEREOF, AND PHARMACEUTICAL COMPOSITION

The present invention provides a tetrahydroprotoberberine compound represented by the formula (I), enantiomers, diastereomers, racemates and mixtures thereof, and pharmaceutically acceptable salts, crystalline hydrates and solvates thereof. The invention also provides a method for preparing the compound and the use thereof in the preparation of a medicament for preventing and/or treating central nervous system diseases.

KHMDS mediated synthesis of 9-arylfluorenes from dibenzothiophene dioxides and arylacetonitriles by tandem SNAr-decyanation-based arylation

A straightforward KHMDS mediated synthetic route to 9-arylfluorenes from readily available starting materials has been developed. This reaction involves SNAr reactions of dioxide with arylacetonitriles, followed by decyanation reaction. The pro

Method for industrially synthesizing desvenlafaxine

The invention provides a method for industrially synthesizing desvenlafaxine. The method is a new technology including the steps that 4-hydroxybenzyl cyanide serves as a starting raw material and is subjected to hydroxyl protection, a condensation reaction, pressurized hydrogenation and an Eschweiler-Clark reaction, and the desvenlafaxine is obtained. The method is small in step number, easy and convenient to operate, high in yield and low in cost, and the product is easy to separate and purify; adopted reagents are all common reagents, and the method is a new technology suitable for industrial production.

Beyond the affinity for protein kinase C: Exploring 2-phenyl-3-hydroxypropyl pivalate analogues as C1 domain-targeting ligands

Over the past fifteen years, we reported the design and synthesis of different series of compounds targeting the C1 domain of protein kinase C (PKC) that were based on various templates. Out of the pivalate templates, 2-[4-(benzyloxy)phenyl]-3-hydroxypropyl pivalate (compound 1) emerged as the most potent and promising PKCα ligand, showing a Ki value of 0.7 μM. In the present contribution our efforts are aimed at better understanding which structural modifications of the pivalate template are allowed for its affinity to the C1 domain of PKC to be preserved or increased. To this aim, thirteen novel analogues of 1 were designed and their interaction with the target was evaluated in silico. Designed compounds were then prepared and fully characterized as well as their affinity for the α and δ isoforms of PKC evaluated. Additionally, in order to investigate the role of chirality in the ligand-target interaction, the pure enantiomers of the most interesting PKC ligands were prepared and their affinity for PKC isoforms was determined. Results from our study revealed that: i) the presence of the ester function seems to be essential for the ligand-target interaction; ii) only a few structural modifications at the ester group are allowed for the C1 domain affinity to be preserved; and iii) the [3H]PDBu replacement experiments showed that the C1 domain of PKC does not exhibit enantiopreference for the pure stereoisomers of tested compounds. Altogether our observations provide further insights into the ligand-target interactions of the PKC C1 domain and represent a step-forward in future development of more specific and effective PKC ligands. This journal is

Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]

This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

One-pot conversion of aldehyde sodium bisulfites into nitriles

Direct conversion of aldehyde sodium bisulfites to the corresponding nitriles can be easily performed by the reaction of an aldehyde sodium bisulfites with a slight execss of hydroxylamine hydrochloride in refluxing toluene and in the presence of 1.0 equivalents of pyridine as catalyst.

Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst

The Lewis acid room temperature ionic liquid, [bmim][InCl4], was found to be an efficient and green catalyst for the highly chemoselective and one-pot conversion of MOM- or EOM-ethers into their corresponding nitriles, bromides, and iodides under microwave irradiation. The procedures are simple, rapid, and high yielding. The catalyst exhibited a remarkable reactivity and is reusable.