4128-32-9

Usage

InChI:InChI=1/C13H16N2O2S/c1-12(2)8-4-5-13(12,3)10(17)15(9(8)16)11-14-6-7-18-11/h6-8H,4-5H2,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 111-71-7 heptanal 
• 111-86-4 n-Octylamine 
• 64-17-5 ethanol 
• 74-85-1 ethene 
• 7214-62-2 2-octyl nitrite 
• 1577-55-5 octadec-9-ene-1,12-diol 
• 111-66-0 oct-1-ene 
• 101-97-3 Ethyl 2-phenylethanoate 
• 111-13-7 hexyl-methyl-ketone 
• 110-43-0 n-pentyl methyl ketone 
• 917-54-4 methyllithium 
• 2747-38-8 methyltrichlorotitanium 
• 41453-02-5 NbMe₂Cl₃ 

Downstream Products

• 15586-11-5 2-chlorocarbonyloxy-octane 
• 18023-52-4 trimethyl-(1-methyl-heptyloxy)-silane 
• 102462-53-3 diphenyl-dithiophosphinic acid-(1-methyl-heptyl ester) 
• 124591-00-0 N,N'-bis-(4-dimethylamino-phenyl)-terephthalamide 
• 24848-81-5 B(O-2-C₈H₁₇)3 
• 111-13-7 hexyl-methyl-ketone 
• 219827-50-6 (2,4,5-trichloro-phenoxy)-acetic acid-(1-methyl-heptyl ester) 
• 103034-34-0 4-nitro-phthalic acid bis-(1-methyl-heptyl ester) 
• 118898-95-6 phthalic acid benzyl ester-(1-methyl-heptyl ester) 
• 599178-04-8 cinnamic acid-(1-methyl-heptyl ester) 
• 2216-41-3 formic acid 1-methyl-heptyl ester 
• 59078-33-0 octan-2-yl 3-phenylpropiolate 
• 70116-81-3 2,4,6-trimethyl-benzoic acid-(1-methyl-heptyl ester) 
• 6319-48-8 carbamic acid-(1-methyl-heptyl ester) 

Relevant academic research and scientific papers

Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex

The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason, the corresponding homogeneous catalytic version with H2 is receiving increasing attention. However, investigation of this alternative has just begun, and several issues are still present, such as the use of noble metals/expensive ligands, high catalytic loading, and poor regioselectivity. Herein, we describe the use of a cheap and easy-To-handle (cyclopentadienone)iron complex (1a), previously developed by some of us, as a precatalyst for the reductive opening of epoxides with H2. While aryl epoxides smoothly reacted to afford linear alcohols, aliphatic epoxides turned out to be particularly challenging, requiring the presence of a Lewis acid cocatalyst. Remarkably, we found that it is possible to steer the regioselectivity with a careful choice of Lewis acid. A series of deuterium labeling and computational studies were run to investigate the reaction mechanism, which seems to involve more than a single pathway.

Supported ionic liquid-like phases as efficient solid ionic solvents for the immobilisation of alcohol dehydrogenases towards the development of stereoselective bioreductions

Polymeric materials containing ionic liquid fragments, like those found in bulk ILs, are excellent solid media for the immobilisation of biocatalysts. Herein, the entrapment of the enzymatic system formed by alcohol dehydrogenase from Rhodococcus ruber (ADH-A) overexpressed in E. coli and its coenzyme has been studied. The activity, stability and reusability of these preparations have been investigated in the bioreduction of prochiral ketones finding excellent levels of conversion and selectivity. Interestingly, the immobilised enzyme remained active and exhibited excellent stability in aqueous solutions after several recycling uses. More importantly, these biopolymer materials retained most of their activity after consecutive reaction cycles, prolonged storage and under flow conditions.

Biocatalytic synthesis of non-vicinal aliphatic diols

Biocatalysts are receiving increased attention in the field of selective oxyfunctionalization of C-H bonds, with cytochrome P450 monooxygenases (CYP450s), and the related peroxygenases, leading the field. Here we report on the substrate promiscuity of CYP505A30, previously characterized as a fatty acid hydroxylase. In addition to its regioselective oxyfunctionalization of saturated fatty acids (ω-1-ω-3 hydroxylation), primary fatty alcohols are also accepted with similar regioselectivities. Moreover, alkanes such as n-octane and n-decane are also readily accepted, allowing for the production of non-vicinal diols through sequential oxygenation. This journal is

Selective palladium nanoparticles-catalyzed hydrogenolysis of industrially targeted epoxides in water

Palladium nanoparticles, with core sizes of ca. 2.5 nm, were easily synthesized by chemical reduction of Na2PdCl4 in the presence of hydroxyethylammonium salts and proved to be efficient for the selective hydrogenolysis of various aromatic, alkylphenyl, aliphatic epoxides in water as green solvent. Capping agents of the metal species were screened to define the most suitable micellar nanoreactors on two target substrates of industrial interest, epoxystyrene and 7,8-epoxy-2-methoxy-2,6-dimethyloctane. In our conditions, the hydrogenolysis of epoxystyrene proved to be pH-dependent, producing either the diol under acidic conditions, or the sweet-smelling 2-phenylethanol in the presence of a base. Promisingly, 7,8-epoxy-2-methoxy-2,6-dimethyloctane was completely and selectively hydrogenated into Florsantol, a sandalwood odorant at a multigram scale (40 g and up to 175g). A general mechanism for the palladium nanoparticles-catalyzed hydrogenolysis of terminal epoxides was proposed according to steric and electronic properties and finely corroborated with deuterium labelling experiments.

The effects of metals and ligands on the oxidation of n-octane using iridium and rhodium “PNP” aminodiphosphine complexes

Ir and Rh “PNP” complexes with different ligands are utilized for the oxidation of n-octane. Based on the obtained conversion, selectivity, and the characterized recovered catalysts, it is found that the combination of Ir and the studied ligands does not promote the redox mechanism that is known to result in selective formation of oxo and peroxo compounds [desired species for C(1) activation]. Instead, they support a deeper oxidation mechanism, and thus higher selectivity for ketones and acids is obtained. In contrast, these ligands seem to tune the electron density around the Rh (in the Rh-PNP complexes), and thus result in a higher n-octane conversion and improved selectivity for the C(1) activated products, with minimized deeper oxidation, in comparison to Ir-PNP catalysts.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water

A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.

Method for synthesizing secondary alcohol in water phase

The invention discloses a method for synthesizing secondary alcohol in a water phase. The method comprises the following steps: taking ketone as a raw material, selecting water as a solvent, and carrying out catalytic hydrogenation reaction on the ketone in the presence of a water-soluble catalyst to obtain the secondary alcohol, wherein the catalyst is a metal iridium complex [Cp * Ir (2, 2'-bpyO)(OH)][Na]. Water is used as the solvent, so that the use of an organic solvent is avoided, and the method is more environment-friendly; the reaction is carried out at relatively low temperature and normal pressure, and the reaction conditions are mild; alkali is not needed in the reaction, so that generation of byproducts is avoided; and the conversion rate of the raw materials is high, and the yield of the obtained product is high. The method not only has academic research value, but also has a certain industrialization prospect.

Four-Coordinated Manganese(II) Disilyl Complexes for the Hydrosilylation of Aldehydes and Ketones with 1,1,3,3-Tetramethyldisiloxane

The coordinatively unsaturated manganase(II) bis(supersilyl) complex Mn[Si(SiMe3)3]2(THF)2 (2) was synthesized in one step via the reaction of MnBr2 with two equivalents of KSi(SiMe3)3 in THF. Complex 2 acts as an effective precatalyst for the catalytic hydrosilylation of aldehydes and ketones with 1,1,3,3-tetramethyldisiloxane (TMDS). The catalytic efficiency can be improved by combining 2 and adamantyl isocyanide (CNAd). The stoichiometric reaction of 2 and two equivalents of CNAd led to the isolation of Mn[Si(SiMe3)3]2(CNAd)2 (3) in high yield. Complex 3 shows superior catalytic performance than 2 in the hydrosilylation of relatively unreactive ketones.

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.