82101-69-7

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 19962-28-8 4-methoxybenzyl phenyl ether 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-01-8 4-Methoxyphenylacetic acid 
• 6258-60-2 p-methoxybenzylmercaptan 
• 104-21-2 p-methoxybenzyl acetate 

Relevant academic research and scientific papers

Method for preparing deuterated compound through decarboxylation and deuteration of carboxylic acid

The invention relates to a method for preparing a deuterated compound through decarboxylation and deuteration of carboxylic acid. According to the method, a carboxylic acid compound is used as a raw material, hydrogen atoms of carboxylate radicals are exc

Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals

Site-specific incorporation of deuterium into drug molecules to study and improve their biological properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon–oxygen bonds

A mild, general, and metal-free method for site-specific deuteration induced by visible light using D2O as the source of deuterium atoms

A radical deuteration procedure using D2O as the source of deuterium atoms is strongly preferred in terms of mildness, sustainability, and cost. Herein, we disclose a radical approach for site-specific, highly efficient and metal-free deuteration using D2O under visible light conditions. This desulfurization-deuteration strategy features mild conditions, broad substrate scope, highly efficient D-incorporation, excellent functional group compatibility, sustainable energy and is hardly affected by substrate steric factors.

Method for deuterating organic matter

The present invention relates to a method of deuterating an organic matter, especially relates to a method of deuterating an organic compound containing a mercapto group or a disulfide bond, and belongs to the technical field of molecular marking. The method of deuterating the organic matter the following steps: dissolving the organic matter in a mixed solvent of an organic solvent and deuterium oxide, adding a phosphine reagent and a free radical initiator, and carrying out a reaction under a light condition for 3-6 h to convert the substrate into a corresponding deuterated product, wherein the organic matter is a thiol, a disulfide or a cysteine-containing polypeptide organic compound. The deuterating method has the characteristics of high deuteration efficiency, good selectivity, good functional group tolerance, high yield, mild reaction conditions, no metals participating in the reaction, wide substrate range and the like, is especially suitable for selectively deuterating the specific position of the carbon chain, and is also suitable for polypeptide substrates.

A convenient method for palladium-catalyzed reductive deuteration of organic substrates using deuterated hypophosphite in D2O

A convenient method for the deuteration of organic substrates using deuterated hypophosphite as the deuterium source was investigated. Transfer deuteration of organic substrates, such as aromatic halides, alkenes, alkynes, epoxides, and O-benzyl derivativ

A new procedure for deconvolution of inter-/intramolecular intrinsic primary and α-secondary deuterium isotope effects from enzyme steady-state kinetic data

The A2B2 flavocytochrome p-cresol methylhydroxylase (PCMH) from Pseudomonas putida oxidizes 4-methylphenol (p-cresol) to 4-hydroxybenzyl alcohol in a process requiring scission of an α-C-H bond with concomitant reduction of covalently bound FAD in each A subunit. Values of k(cat)/K were determined from steady-state kinetic data for the reactions of PCMH with the following substrates: 4-methylphenol, 4-(2H1)methylphenol, 4- (2H2)methylphenol, and 4-(2H3)methylphenol. A procedure was devised to extract the intrinsic primary deuterium and intrinsic α-secondary deuterium kinetic isotope effects from these values of k(cat)/K. The primary effect, P, is 6.71 ± 0.08, and the secondary effect, S, is 1,013 ± 0.014. The magnitudes of these effects are discussed in terms of an early or late transition state, hydrogen tunneling, coupled motion between the leaving and remaining hydrogens of the methyl group, and a H- expulsion mechanism versus a substrate radical mechanism versus a covalent substrate-FAD intermediate mechanism. The reaction of 4-ethylphenol with PCMH produces 4-vinylphenol and (-)-S-1-(4-hydroxyphenyl)ethanol (~100% enantomeric excess). The evidence indicates that these are formed from a common intermediate, presumably a p- quinone methide. From the partition ratios for the formation of the alcohol and 4-vinylphenol from 4-ethylphenol, 4-(1',1'-2H2)ethylphenol, and 4- (2',2',2'-2H3)ethylphenol, the primary isotope effect for conversion of the p-quinone (2',2',2'2H3)methide to 4-(2',2'-2H2)vinylphenol was estimated to be about 2, and the α-secondary isotope effect for conversion of p- quinone (1'-2H1)methide to 1-(4-hydroxyphenyl)-(1'-2H1)ethanol was found to be inverse (=0.83), as expected for sp2 to sp3 hybridization change at the α-carbon. Values of k(cat)/K were determined for 4-ethylphenol, R,S- (±)-4-(1'-2H1)ethylphenol (abbreviated R,S-D), S-(-)-4-(1'- 2H1)ethylphenol (S-D), R-(+)- 4-(1'-2H1)ethylphenol (R-D), and 4- (1',1',2H2)ethylphenol (D2). The (D2)(k(cat)/K) value was found to be 5.1- 6.1, the same as determined in an earlier study. Unexpectedly, the values for (R,S-D)(k(cat)/K), (S-D)(k(cat)/K), and (R-D)(k(cat)/K) were all about the same (~1.7), indicating that there is nearly an equal probability for pro-R or pro-S C-H bond scission. An apparent flux ratio for the pro-S path/pro-R path was estimated to be 0.78 ± 0.02. The same procedure devised to determine values for P and S for 4-methylphenol was used to determine these values for the 4-ethylphenol reaction (commitment to catalysis = 0); P = 5.98 ± 0.12 and S = 0.967 ±0.021. These values are essentially the same as those determined for 4-methylphenol. Thus, the chemical mechanisms for both substrates are assumed to be similar.

Reductive lithiation of arylalkyl methyl ethers

We have investigated the reductive cleavage of arylalkyl methyl ethers with an excess of lithium metal and a catalytic amount of naphthalene. The reaction proceeds regioselectively in the presence of various substituents on the aromatic ring, allowing access to a wide array of arylalkyl lithium derivatives some of which are not easily accessible by conventional methods.

Side Chain Hydroxylation of Aromatic Compounds by Fungi. Part 4. Influence of the para Substituent on Kinetic Isotope Effects During Benzylic Hydroxylation by Mortierella isabellina

The benzylic hydroxylation of a series of para-substituted toluenes by the fungus Mortierella isabellina has been studied by using CD3, CHD2, and CH2D methyl labelled substrates.Inter- and intramolecular primary and secondary deuterium kinetic isotope effect ratios have been determined: the intermolecular primary effects are maximal with strongly electron-withdrawing para substituents (R = CN and CF3), while the intramolecular primary effects are minimal for R = H but increase in instances where R is electron donating or withdrawing.These results are interpreted in terms of a dependence of the hydroxylation mechanism on the nature of the para substituent.

Reductive Displacement of the Acetate Group in Allyl, Propargyl, and Benzyl Acetates by NaBH4/NiCl2 * 6H2O

The combination of NiCl2 *6H2O and NaBH4 provides an effective system for reductive removal of the acetate group of allyl, propargyl, and benzyl acetates.Sterically less hindered allyl acetates are converted preferentially to the corresponding alkanes (Table 1).