55815-72-0

Upstream product

• 1111-72-4 carbon dioxide 
• 824-94-2 p-methoxybenzyl chloride 
• 215739-05-2 <13C>-4-methoxybenzyl cyanide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 100-42-5 styrene 
• 42766-36-9 potassium p-methoxyphenylacetate 

Downstream Products

• 215653-77-3 4-methoxybenzyl-2',4'-dihydroxyphenyl [13C]ketone 
• 55815-73-1 [¹³C₁]-ethyl 2-(4-methoxyphenyl)acetate 
• 208644-97-7 C₂₃⁽¹³⁾CH₃₀O₁₂ 
• 208645-00-5 [8-13C]-cornoside 
• 208645-06-1 C₁₃⁽¹³⁾CH₂₄O₈ 
• 208644-98-8 [8-13C]-salidroside 
• 208644-96-6 C₉⁽¹³⁾CH₁₂O₃ 
• 208644-94-4 C₈⁽¹³⁾CH₁₀O₃ 
• 208644-95-5 [8-13C]-4-hydroxyphenylethanol 
• 215653-78-4 4'-methoxybenzyl-7-hydroxy-[4-13C]isoflavone 
• 208644-93-3 C₇⁽¹³⁾CH₈O₃ 

Relevant academic research and scientific papers

Photochemical Strategy for Carbon Isotope Exchange with CO2

A photocatalytic approach for carbon isotope exchange is reported. Utilizing [13C]CO2 and [14C]CO2 as primary C1 sources, this protocol allows the insertion of the desired carbon isotope into phenyl acetic acids without the need for structural modifications or prefunctionalization in one single step. The exceptionally mild conditions required for this traceless transformation are in stark contrast with those for previous methods requiring the use of harsh thermal conditions.

Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis

Carbazole/cyanobenzene photocatalysts promote the direct isotopic carboxylate exchange of C(sp3) acids with labeled CO2. Substrates that are not compatible with transition-metal-catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabeling of drug molecules and precursors with [11C]CO2 is demonstrated.

Direct reversible decarboxylation from stable organic acids in dimethylformamide solution

Many classical and emerging methodologies in organic chemistry rely on carbon dioxide (CO2) extrusion to generate reactive intermediates for bond-forming events. Synthetic reactions that involve the microscopic reverse-the carboxylation of reactive intermediates-have conventionally been undertaken using very different conditions. We report that chemically stable C(sp3) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution. Decarboxylation-carboxylation occurs with substrates resistant to protodecarboxylation by Br?nsted acids under otherwise identical conditions. Isotopically labeled carboxylic acids can be prepared in high chemical and isotopic yield by simply supplying an atmosphere of 13CO2 to carboxylate salts in polar aprotic solvents. An understanding of carboxylate reactivity in solution enables conditions for the trapping of aldehydes, ketones, and a,b-unsaturated esters.

Transition-Metal-Free Carbon Isotope Exchange of Phenyl Acetic Acids

A transition-metal-free carbon isotope exchange procedure on phenyl acetic acids is described. Utilizing the universal precursor CO2, this protocol allows the carbon isotope to be inserted into the carboxylic acid position, with no need of precursor synthesis. This procedure enabled the labeling of 15 pharmaceuticals and was compatible with carbon isotopes [14C] and [13C]. A proof of concept with [11C] was also obtained with low molar activity valuable for distribution studies.

Generation of stoichiometric ethylene and isotopic derivatives and application in transition-metal-catalyzed vinylation and enyne metathesis

Ethylene is one of the most important building blocks in industry for the production of polymers and commodity chemicals. 13C- and D-isotope-labeled ethylenes are also valuable reagents with applications ranging from polymer-structure determination, reaction-mechanism elucidation to the preparation of more complex isotopically labeled compounds. However, these isotopic derivatives are expensive, and are flammable gases, which are difficult to handle. We have developed a method for the controlled generation of ethylene and its isotopic variants including, for the first time, fully isotopically labeled ethylene, from simple alkene precursors by using Ru catalysis. Applying a two-chamber reactor allows both the synthesis of ethylene and its immediate consumption in a chemical transformation permitting reactions to be performed with only stoichiometric amounts of this two carbon olefin. This was demonstrated in the Ni-catalyzed Heck reaction with aryl triflates and benzyl chlorides, as well as Ru-mediated enyne metathesis. Why more when less works! A method for the controlled generation of ethylene including the fully isotopically labeled derivative is described, as well as their use in three transition-metal-catalyzed reactions. Applying a two-chamber reactor, only stoichiometric amounts of ethylene are required, which allows the simple installment of deuterium and 13C in the product (see scheme).

Synthesis of [4-13C]-isoflavonoid phytoestrogens

Efficient syntheses are described for 13C-labelled derivatives of the isoflavonoid phytoestrogens, genistein, biochanin A, daidzein and formononetin, for use in metabolic studies. The synthetic procedure employs 13C-labelled cyanide as the source of the label to produce the isoflavones with a single 13C atom at the C-4 position. (C) 2000 Elsevier Science Ltd.

Synthesis of 13C-labeled possible intermediates in the biosynthesis of phenylethanoid derivatives, cornoside and rengyosides

In order to clarify the biosynthetic pathway of C6-C2 unit compounds containing salidroside, cornoside, and rengyosides A and B in oleaceous plants, 13C-labeled putative precursors, 4-hydroxyphenylethanol, salidroside and cornoside, were prepared.

Synthesis of 13C labelled daidzein and formononetin.

Efficient methods are described for the synthesis of daidzein and formononetin labelled with a single 13C atom at the 4-position, to prepare material for metabolic studies.