6329-73-3

Usage

Uses

Used in Scientific Research:
1-(3,4-Methylenedioxyphenyl)ethanol is used as a reference standard in forensic and toxicological analysis for the identification and quantification of psychoactive substances.
Used in Forensic Analysis:
MDPHP is used as a reference compound in forensic analysis to help identify and characterize designer drugs and their potential involvement in criminal cases.
Used in Toxicological Analysis:
1-(3,4-Methylenedioxyphenyl)ethanol is used in toxicological analysis to study the effects of psychoactive substances on human health and to determine their potential for causing acute toxicity and addiction.

InChI:InChI=1/C9H10O3/c1-6(10)7-2-3-8-9(4-7)12-5-11-8/h2-4,6,10H,5H2,1H3

Upstream product

• 120-57-0 piperonal 
• 74-88-4 methyl iodide 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 75-24-1 trimethylaluminum 
• 917-54-4 methyllithium 
• 74-83-9 methyl bromide 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 71095-27-7 1-(2′-bromo-4′,5′-methylenedioxyphenyl)ethan-1-ol 
• 203937-16-0 dimethyl 9-(4-fluorophenyl)-6-methylnaphtho[1,2-d]-1,3-dioxole-7,8-dicarboxylate 
• 179237-91-3 (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol 
• 1374418-57-1 (E)-1-(4-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)phenyl)ethanone 
• 1374418-58-2 (E)-4-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)benzonitrile 
• 40288-65-1 1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone 
• 126266-78-2 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one 
• 121734-64-3 1-benzo[1,3]dioxol-5-yl-ethylamine 
• 6808-65-7 Dubamine 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 1384560-04-6 1-(benzo[d][1,3]-dioxol-5-yl)-3-(2-bromophenyl)propan-1-ol 

Relevant academic research and scientific papers

Optimization of asymmetric reduction conditions of 1-(benzo [d] [1,3] dioxol-5-yl) ethanone by Lactobacillus fermentum P1 using D-optimal experimental design-based model

The biocatalytic asymmetric reduction of prochiral ketones is a significant transformation in organic chemistry as chiral carbinols are biologically active molecules and may be used as precursors of many drugs. In this study, the bioreduction of 1-(benzo [d] [1,3] dioxol-5-yl) ethanone for the production of enantiomerically pure (S)-1-(1,3-benzodioxal-5-yl) ethanol was investigated using freeze-dried whole-cell of Lactobacillus fermentum P1 and the reduction conditions was optimized with a D-optimal experimental design-based optimization methodology. This is the first study using this optimization methodology in a biocatalytic asymmetric reduction. Using D-optimal experimental design-based optimization, optimum reaction conditions were predicted as pH 6.20, temperature 30 °C, incubation time 30 h, and agitation speed 193 rpm. For these operating conditions, it was estimated that the product could be obtained with 94% enantiomeric excess (ee) and 95% conversion rate (cr). Besides, the actual ee and cr were found to be 99% tested under optimized reaction conditions. These findings demonstrated that L. fermentum P1 as an effective biocatalyst to obtain (S)-1-(1,3-benzodioxal-5-yl) ethanol and with the D-optimal experimental design-based optimization, this product could be obtained with the 99% ee and 99% cr. Finally, the proposed mathematical optimization technique showed the applicability of the obtained results for asymmetric reduction reactions.

Indium-Catalyzed Formal Carbon-Halogen Bond Insertion: Synthesis of α-Halo-α,α-disubstituted Esters from Benzylic Halides and Diazo Esters

One-carbon-unit insertion into carbon-halogen (C-X) bonds accompanied by the formation of a new C-X bond and carbon-chain elongation is a powerful synthetic method of complex organohalides. Herein, we developed an indium trihalide catalyzed formal insertion of diazo esters into a C-X (X = Cl, Br, I) bond. In the present system, the reactions of α-aryl diazo esters with benzylic chlorides, bromides, and iodides yielded α-chloro, α-bromo, and α-iodo esters, respectively.

Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2

Abstract: Chiral heterocyclic secondary alcohols have received much attention due to their widespread use in pharmaceutical intermediates. In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asymmetric reduction of prochiral ketones to chiral secondary alcohols. Secondary chiral carbinols were obtained by asymmetric bioreduction of different prochiral substrates with results up to > 99% enantiomeric excess (ee). (R)-1-(benzofuran-2-yl)ethanol 5a, which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective β-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70?g of (R)-5a in enantiomerically pure form was obtained in 96% yield. Also, production of (R)-5a in terms of yield and gram scale through catalytic asymmetric reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcohols compared to chemical processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis. Graphical Abstract: [Figure not available: see fulltext.]

Postsynthetic Modification of Half-Sandwich Ruthenium Complexes by Mechanochemical Synthesis

A mild and environmentally friendly method to synthesize half-sandwich ruthenium complexes through the Wittig reaction between an aldehyde-tagged half-sandwich ruthenium complex and phosphorus ylide mechanochemically is reported herein. The mechanochemical synthesis of valuable half-sandwich ruthenium complexes resulted in a fast reaction, good yield with simple workup, and the avoidance of harsh reaction conditions and organic solvents. The synthesized half-sandwich ruthenium complexes exhibited high catalytic activity for transfer hydrogenation of ketones using 2-propanol as the hydrogen source and solvent. Density functional theory was carried out to propose a mechanism for the transfer hydrogenation process. The modeling suggests the importance of the labile p-cymene ligand in modulating the reactivity of the catalyst.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

FUSED GLYCOSIDASE INHIBITORS

Compounds of formula (I), wherein A, Z, E, R1, R2, m and n have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.

Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier

Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.

Reduction over Condensation of Carbonyl Compounds through a Transient Hemiaminal Intermediate Using Hydrazine

Reduction of carbonyl moieties to the corresponding alcohol using simply hydrazine hydrate has been considerably unfeasible until now due to the well-known condensation reaction. However, herein, we report that using an excess of 20-fold equivalents, the reduction proceeds in excellent yields. 1H NMR study of the reaction and density functional theory (DFT) calculations indicate that the final fate of the hemiaminal intermediate is crucial to obtain the alcohol or the hydrazone.

RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.

Asymmetric Deoxygenative Cyanation of Benzyl Alcohols Enabled by Synergistic Photoredox and Copper Catalysis?

Summary of main observation and conclusion. An enantioselective deoxygenative cyanation of benzyl alcohols was accomplished for the first time through the synergistic photoredox and copper catalysis. This reaction features the use of organic photosensitizer and low-cost 3d metal catalyst, simple and safe operations, and extremely mild conditions. A variety of chiral benzyl nitriles were produced in generally good yields and high level of enantiocontrols from readily available feedstocks (22 examples, up to 93% yield and 92% ee).