14353-75-4

Upstream product

• 334-48-5 1-decanoic acid 
• 108-95-2 phenol 
• 112-13-0 n-decanoyl chloride 
• 112-31-2 caprinaldehyde 
• 98-80-6 phenylboronic acid 
• 112-05-0 nonanoic acid 

Downstream Products

• 14353-77-6 1-(4-hydroxy-phenyl)-decan-1-one 
• 14353-76-5 1-(2-hydroxy-phenyl)-decan-1-one 
• 25360-32-1 carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) 
• 61817-37-6 RuH(η5-OC6H5)(PPh3) 
• 6048-82-4 decanophenone 
• 15473-32-2 decananilide 
• 66606-02-8 p-methyldecanophenone 
• 1162025-31-1 bis(2-hydroxy-5-n-decylphenyl)methane 
• 111-84-2 nonane 
• 34557-54-5 methane 
• 91583-66-3 phenoxotris(triphenylphosphine)cobalt(I) 
• 112-12-9 methyl nonyl ketone 
• 77635-20-2 5-decylsalicylaldehyde 
• 2985-57-1 4-decylphenol 

Relevant academic research and scientific papers

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Palladium-Catalyzed Aerobic Oxidative Coupling of Amides with Arylboronic Acids by Cooperative Catalysis

The first fluoride and palladium co-catalyzed conversion of amide to ester through an aerobic oxidative coupling pathway is reported. This new approach presents a practical process that employs easily available oxygen and commercially available arylboronic acids as coupling partners, uses a wide range of N- tosylamides, and proceeds under mild reaction conditions. This protocol demonstrates broad functional group tolerance, and provides an alternative option to synthesize esters from N-tosylamides which obtained by simply N-functionalization of secondary amides.

Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions

A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.

Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2

A novel, in-situ synthesis of dichlorotriphenylphosphorane (Ph3PCl2) is accomplished upon combining PPh3and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl2). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et2NH or CH2N2results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.

Organocatalytic oxidation of aldehydes to mixed anhydrides

TEMPO catalyzes the direct oxidation of aldehydes to mixed anhydrides in the presence of a carboxylic acid. The anhydrides can be converted in situ to esters, secondary, tertiary or Weinreb amides in high yield. Oxidation of the aldehyde directly to 2-propyl esters is also possible using only catalytic amounts of acid. The oxidation reactions are rapid and take place under mild conditions.

Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines

Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

Synthesis, antimicrobial evaluation, QSAR and in silico ADMET studies of decanoic acid derivatives

Various derivatives of decanoic acid (CD) have been synthesized and evaluated against Gram positive B. subtilis, S. aureus and Gram negative E. coli bacteria as well as against fungi C. albicans and A. niger. Quantitative structure activity relationship (QSAR) models for antimicrobial activities were developed using multiple linear regression and cross validated by leave one out (LOO) approach. QSAR studies indicated that activity against Gram positive bacteria was governed by lipophilicity of the compounds while topological steric nature of the molecule was deciding factor for antifungal activity. Further, in silico ADMET studies showed that compounds CD12, 19, 20 and 23 could be explored further for other activities.

Synthesis and critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants

A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.

An eco-friendly method for the synthesis of aryl and alkyl esters of carboxylic acids using acid activated Indian bentonite

Esterification of various carboxylic acids with phenol and alcohols has been achieved using acid activated Indian bentonite (AAIB) as catalyst. The catalyst is versatile, and the reaction is found to work well for primary, secondary and tertiary alcohols. The yields are very good under specific reaction conditions.

Cytotoxicity and antiestrogenicity of a novel series of basic diphenylethylenes

On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.