1851-93-0

Upstream product

• 1674-38-0 dodecanophenone 
• 4292-19-7 1-Iodododecane 
• 100-52-7 benzaldehyde 
• 15288-76-3 1-Benzoyl-undecin-⁽¹⁰⁾ 
• 1334446-76-2 (1-methoxydodecyl)triphenylphosphonium trifluoromethanesulfonate 
• 100-58-3 phenylmagnesium bromide 
• 14620-52-1 1,1-dimethoxy-dodecane 
• 112-30-1 1-Decanol 
• 98-86-2 acetophenone 
• 98-85-1 1-Phenylethanol 
• 143-07-7 lauric acid 
• 65-85-0 benzoic acid 
• 15327-70-5 1-Phenyl-dodecin-⁽¹¹⁾-ol-⁽¹⁾ 

Downstream Products

• 1674-38-0 dodecanophenone 
• 270076-47-6 (R)-1-phenyl-1-dodecanol 
• 125653-73-8 1-phenyldodecyl acetate 
• 270076-41-0 (S)-1-phenyl-1-dodecanol 

Relevant academic research and scientific papers

Ligand-free Guerbet-type reactions in air catalyzed by in situ formed complexes of base metal salt cobaltous chloride

Inexpensive, earth-abundant and environmentally benign cobaltous chloride efficiently accomplishes the catalytic β-alkylation of alcohols in air at 140 °C. At higher loadings of cobaltous chloride (1 mol%) in the presence of 2.5 mol% NaOtBu, there is a rapid formation of heterogeneous Co nanoparticles (NPs) which are apparently sensitive to air and result in poor yields (ca. 25%) of β-alkylated products. In contrast, performing the reaction in an argon atmosphere under otherwise identical conditions leads to higher yields (ca. 44%). The heterogenization and eventual loss of activity in air could be delayed by operating at a lower (0.01 mol%) CoCl2 loading in the presence of 2.5 mol% NaOtBu at 140 °C. Under these conditions, the catalytic β-alkylation of alcohols proceeded with high yields (up to 89%) and unprecedented turnovers (ca. 8900). Mechanistic studies are indicative of the involvement of catalysts based on in situ generated molecular Co complexes of alcohols. Labelling studies provide key evidence for the involvement of C-H activation in the cobaltous chloride catalyzed β-alkylation with a KIE of 1.61. Kinetic studies indicate linear dependence of the rate on the concentration of cobaltous chloride and sodium t-butoxide along with a non-linear dependence on the concentration of 1-phenyl ethanol and benzyl alcohol.

Mn(i) phosphine-amino-phosphinites: a highly modular class of pincer complexes for enantioselective transfer hydrogenation of aryl-alkyl ketones

A series of Mn(i) catalysts with readily accessible and more π-accepting phosphine-amino-phosphinite (P′(O)N(H)P) pincer ligands have been explored for the asymmetric transfer hydrogenation of aryl-alkyl ketones which led to good to high enantioselectivities (up to 98%) compared to other reported Mn-based catalysts for such reactions. The easy tunability of the chiral backbone and the phosphine moieties makes P′(O)N(H)P an alternative ligand framework to the well-known PNP-type pincers.

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.

Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts

The catalytic alkylation of ketones with alcohols via the hydrogen borrowing methodology (HB) has the potential to be a highly efficient approach for forming new carbon-carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity. Other factors-base, base loading, solvent and reaction temperature-were also investigated to tune the selectivity further. The optimised conditions were used to demonstrate the scope of the reaction across 17 ketones and 14 alcohols containing a variety of functional groups. A series of mechanistic investigations were performed to probe the reasons behind the product selectivity, including kinetic and deuterium studies.

PROCESS FOR THE PREPARATION OF ALKOXYLATES COMPOSITIONS

A mixture of two alkoxylates surfactants, one being an aryl aliphatic carbinol alkoxylate, the other one being a dialiphatic carbinol alkoxylate, said mixture being useful for stabilizing emulsions and dispersions used in agricultural or pharmaceutical formulations. The alkoxylates surfactants may serve as substitutes for nonylphenol ethoxylates (NPE) and tristyrylphenol ethoxylates (TSE).

Expanding substrate scope of lipase-catalyzed transesterification by the utilization of liquid carbon dioxide

Secondary alcohols having bulky substituents on both sides of the chiral center are often poor substrates for most lipases. Here we reported that substrate scopes of two of the most used lipases, Candida antarctica lipase B and Burkholderia cepacia lipase, were found to be expanded toward more bulky secondary alcohols such as 1-phenyl-1-dodecanol and 2-methyl-1-phenyl-1-propanol by simply using them in liquid carbon dioxide as a solvent. The effects of solvents, reaction pressure, and pre-treatment of the enzyme with liquid CO2on this acceleration phenomenon were also studied.

Effects of phosphorus substituents on reactions of α- alkoxyphosphonium salts with nucleophiles

The effects of phosphorus substituents on the reactivity of α-alkoxyphosphonium salts with nucleophiles has been explored. Reactions of α-alkoxyphosphonium salts, prepared from various acetals and tris(o-tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high-yielding nucleophilic substitution reactions of α-alkoxyphosphonium salts. The reactivity of these salts was determined by a balance between steric and electronic factors, respectively, represented by cone angles θ and CO stretching frequencies ν (steric and electronic parameters, respectively). In addition, a novel reaction of α-alkoxyphosphonium salts derived from Ph3P with Grignard reagents was observed to take place in the presence of O2 to afford alcohols in good yields. A radical mechanism is proposed for this process that has gained support from isotope-labeling and radical-inhibition experiments. A dramatic change in the reactivity of an α-alkoxyphosphonium salt toward nucleophiles is observed due to the steric and electronic nature of the phosphine substituents. By changing the type of phosphorus substituents, the reaction pathway can be controlled to proceed selectively by substitution or a new radical reaction (see scheme; OTf=trifluoromethansulfonate, TMS=trimethylsilyl, o-tol=tolyl). Copyright

Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution

The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C11-C19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enan

An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O2 atmosphere

An unusual and novel reaction of α-alkoxyphosphonium salts, generated from O,O-acetals and Ph3P, with Grignard reagents under an O 2 atmosphere afforded alcohols in moderate to high yields. It was clarified by isotopic labelling experiments that the reaction proceeded via a novel radical pathway.

Sulfonylated aminothiazoles as new small molecule inhibitors of protein phosphatases

Based on a previously identified lead structure, SC-ααδ9, we have developed a versatile new chemical scaffold that can be readily modified to generate libraries of both Tyr and dual specificity phosphatase inhibitors with reduced molecular weight and lipophilicity. The most potent analogue identified to date, aminothiazole 8z, inhibits the dual specificity phosphatase Cdc25B with a Ki of 4.6 ± 0.4 μM and a Hill coefficient of 2.