50530-16-0

Upstream product

• 108-85-0 1-bromocyclohexane 
• 1111-72-4 carbon dioxide 
• 1641-69-6 [13C]Carbon monoxide 
• 110-83-8 cyclohexene 
• 931-50-0 cyclohexylmagnesium bromide 
• 542-18-7 cyclohexyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 

Downstream Products

• 349651-62-3 C₉⁽¹³⁾C₂H₁₈O₂ 
• 349651-63-4 C₇⁽¹³⁾C₂H₁₅Br 
• 87803-56-3 C₆⁽¹³⁾CH₁₂O 

Relevant academic research and scientific papers

Synthesis of Carbon-13 Labelled Carboxylic Acids via Organoborane Reactions

13C-Labelled carboxylic acids are readily synthesized via the reaction of organoboranes with 13C-enriched carbon monoxide; functionally substituted acids are efficiently prepared via a carbonylation-oxidation sequence.

New type II manumycins produced by Streptomyces nodosus ssp. asukaensis and their biosynthesis

Five new type II manumycins, containing the hydroxyquinol mC7N unit, asukamycins A-II, B-II, C-II, D-II, E-II, were discovered in cultures of Streptomyces nodosus ssp. asukaensis. The biosynthetic origin of the type II manumycins from the type 'I compounds, containing an epoxyquinol mC7N unit, was deduced from the time course of production and proven by preparing [7′-13C]asukamycin A and demonstrating its incorporation into asukamycin A-II.

Catalytic Decarboxylation/Carboxylation Platform for Accessing Isotopically Labeled Carboxylic Acids

An integrated catalytic decarboxylation/carboxylation for accessing isotopically labeled carboxylic acids with13CO2 or14CO2 is described. The method shows a wide scope under mild conditions, even in the context of late-stage functionalization, and does not require stoichiometric organometallics, thus complementing existing carbon-labeling techniques en route to carboxylic acids.

Carbon dioxide as a C1 building block for the formation of carboxylic acids by formal catalytic hydrocarboxylation

A happy marriage of two processes: An effective catalytic system was identified for the direct synthesis of carboxylic acids from non-activated olefins or alcohols, CO2, and H2. Detailed analysis together with labeling studies indicated that the overall hydrocarboxylation of simple olefins results from a combination of the reverse water-gas shift (rWGS) reaction and a hydroxycarbonylation step, each promoted by a rhodium catalyst (see scheme). Copyright

Biosynthesis of phoslactomycins: Cyclohexanecarboxylic acid as the starter unit

Phoslactomycins (PLMs) A-F, produced by actinomycetes are polyketide-type antibiotics derived from a hydroxycyclohexanecarboxylic acid or a cyclohexanecarboxylic acid starter unit. Feeding experiments with [2- 13C]shikimic acid indicated that the C-18 carbon of PLMs comes from C-5 of shikimate. Further feeding studies of cis and trans-3-hydroxy[7- 13C]cyclohexanecarboxylic acid, [7-13C]- and [ 2H11]cyclohexanecarboxylic acid have suggested that the starter unit in the PLM biosynthesis is not cis-3-hydroxycyclohexanecarboxylate but cyclohexanecarboxylate and that PLM-B is produced initially, and subsequently converted to other analogs by hydroxylation and acylation.

Biosynthesis of the cyclohexanecarboxylic acid starter unit of ω-Cyclohexyl fatty acids in alicyclobacillus acidocaldarius

The formation of the cyclohexanecarboxylic acid starter unit of ω-cyclohexyl fatty acids from shikimic acid in Alicyclobacillus acidocaldarius (formerly Bacillus acidocaldarius) has been studied. Feeding experiments with 13C- and 2H-labeled samples of shikimic acid and potential intermediates in the wild type and two blocked mutants demonstrated that the formation of cyclohexanecarboxylic acid in this organism follows the same pathway as in Streptomyces collinus (J. Am. Chem. Soc., preceding paper in this issue). (15,3S)-3-Hydroxycyclohexanecarboxylic acid (20) is accumulated by blocked mutant 2, indicating that 5-hydroxycyclohex-l-enecarboxylic acid (6) is first reduced to the hydroxy acid 20 and then dehydrated to 2-cyclohexenecarboxylic acid (8). A sample of [6-2H1]shikimic acid was fed to blocked mutant 2. Deuterium occupied the pro-2S position in the resultant 20, which was then lost when 20 was refed to blocked mutant 10. Thus, the dehydration of 20 involves the removal of the nonacidic pro-25 proton and the C-3 hydroxyl group in an anti fashion. The stereochemistries of other transformations along the pathway are also discussed.