82053-13-2

Upstream product

• 930-68-7 cyclohexenone 
• 7677-24-9 trimethylsilyl cyanide 
• 822-67-3 Cyclohex-2-enol 

Downstream Products

• 615265-44-6 1-[(methylthio)methoxy]cyclohex-2-ene-1-carbonitrile 
• 25017-78-1 3-cyano-2-cyclohexenone 

Relevant academic research and scientific papers

Stereoselective cyanosilylation reactions in hindered cyclic ketones

An efficient, mild and inexpensive protocol for the stereoselective construction of cyanohydrins in hindered, and in some cases, multifunctional cyclic ketones has been established.

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

Synthesis of cyanooxovanadate and cyanosilylation of ketones

The cyanosilylation was performed by using metavanadate catalysts, and in situ measurements revealed the formation of [VO2(CN)3]2- and [VO4TMS2]- under reaction conditions. The reaction of [VO2(CN)3]2-, trimethylsilyl cyanide (TMSCN), and water afforded [

Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade

The cyanosilylation of carbonyl compounds is a fundamental reaction in organic synthesis, to give cyanohydrins. Ketones are particularly reluctant to cyanosilane addition and require the action of a catalyst, and despite many soluble Br?nsted and Lewis ac

Mechanism-Based inactivation of human cytochrome p450 3A4 by two piperazine-Containing compounds

Human cytochrome P450 3A4 (CYP3A4) is responsible for the metabolism of more than half of pharmaceutic drugs, and inactivation of CYP3A4 can lead to adverse drug-drug interactions. The substituted imidazole compounds 5-fluoro-2-[4-[(2-phenyl-1H-imidazol-5-yl) methyl]-1-piperazinyl]pyrimidine (SCH 66712) and 1-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine (EMTPP) have been previously identified as mechanism-based inactivators (MBI) of CYP2D6. The present study shows that both SCH 66712 and EMTPP are also MBIs of CYP3A4. Inhibition of CYP3A4 by SCH 66712 and EMTPP was determined to be con-centration, time, and NADPH dependent. In addition, inactivation of CYP3A4 by SCH 66712 was shown to be unaffected by the presence of electrophile scavengers. SCH 66712 displays type I binding to CYP3A4 with a spectral binding constant (Ks) of 42.9 ± 2.9 μM. The partition ratios for SCH 66712 and EMTPP were 11 and 94, respectively. Whole protein mass spectrum analysis revealed 1:1 binding stoichiometry of SCH 66712 and EMTPP to CYP3A4 and a mass increase consistent with adduction by the inactivators without addition of oxygen. Heme adduction was not apparent. Multiple monooxygenation products with each inactivator were observed; no other products were apparent. These are the first MBIs to be shown to be potent inactivators of both CYP2D6 and CYP3A4.

Cyanosilylation of carbonyl compounds with trimethylsilyl cyanide catalyzed by an yttrium-pillared silicotungstate dimer

An yttrium-pillared silicotungstate dimer (see picture) catalyzes the cyanosilylation of structurally diverse ketones and aldehydes with trimethylsilyl cyanide (TMSCN). The reactions proceed selectively and afford the corresponding cyanohydrin trimethylsi

Mild and efficient trimethylsilylcyanation of ketones catalysed by PNP chloride

Mild & green: The commercially and readily available PNPCl behaves as a very effective catalyst for the synthesis of various trimethylsilyl cyanohydrins from a wide range of aliphatic, cyclic, α,β-unsaturated and aromatic ketones. The method proceeds at r

Dauben-Michno oxidative transposition of allylic cyanohydrins - Enantiomeric switch of (-)-carvone to (+)-carvone

Allylic cyanohydrins were subjected to Dauben-Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (-)-carvone to its enantiomer.

Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient catalysts for the cyanosilylation and cyanocarbonation of aldehydes and ketones

A variety of aldehydes and ketones were transformed to their corresponding cyanohydrin silyl ethers in good to excellent yields in the presence of 1-5 mol% of tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP). Cyanohydrin carbonates were also readily prepared using 5-10 mol% of TTMPP as an organocatalyst.

Alkali salt of L-proline as an efficient and practical catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions

The alkali salt of L-proline was demonstrated to be an efficient and practical catalyst for the cyanosilylation of a wide variety of simple and functionalized carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the corresponding cyanohydrins in good to excellent yields. Copyright Taylor & Francis Group, LLC.