66806-69-7

Upstream product

• 108-94-1 cyclohexanone 
• 78-84-2 isobutyraldehyde 
• 72653-51-1 2-(1-phenylthio-2-methylpropyl)cyclohexanone 
• 43108-68-5 2-(1-Hydroxy-2-methylpropyl)cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 4471-09-4 N-benzylcyclohexylimine 
• 94348-72-8 2-(1-hydroxy-2-methylpropyl)-2-cyclohexen-1-one 

Downstream Products

• 117712-81-9 2-(1-Isopropyl-but-3-enyl)-cyclohexanone 
• 117712-82-0 1-Allyl-2-[2-methyl-prop-(E)-ylidene]-cyclohexanol 
• 129905-56-2 ethyl-3-(1-cyclohexenyl)-4-methyl pentenoate 
• 4668-64-8 2-(2-methylpropyl)cyclohexanone 
• 129905-54-0 2-isobutylidene-1-cyclohexanol 
• 117712-74-0 (1S,1'S)-2,2'-Bis-[2-methyl-prop-(E)-ylidene]-bicyclohexyl-1,1'-diol 

Relevant academic research and scientific papers

Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis

The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.

Phosphoric acid mediated tautomerism of imines: Addition of a secondary enamine intermediate to aldehydes

A phosphoric acid derivative has been shown to promote the addition between an imine and several aldehyde substrates through an enamine intermediate to give cross-aldol condensation products. The reaction scope and preliminary mechanistic investigations will be presented.

Remarkably chemoselective reduction of unmodified Baylis-Hillman adducts by InCl3/NaBH4: Application to the stereoselective synthesis of trisubstituted alkenones including two alarm pheromones

A novel, convenient and solely stereoselective synthesis of trisubstituted E-alkenones has been achieved by InCl3/NaBH4 mediated chemoselective reduction of unmodified Baylis-Hillman adducts derived from vinyl ketones and cycloalkenones for the first time. The efficiency of this methodology in the practical synthesis of (S)-(+)-manicone and (S)-(+)-normanicone, two alarm pheromones of Manica ants, has been demonstrated. Georg Thieme Verlag Stuttgart.

An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone

2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective β-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.

Stereochemistry of Addition of Allylic Grignard Reagents to α,β-Ethylenic Ketones

The stereochemistry of the addition of allylic Grignard reagents, (mainly crotylmagnesium chloride) to various conjugated enones has been investigated and a compact transition state is postulated.For s-cis-enones bearing no bulky substituents, a boat transition state, involving a trans-crotylmagnesium chloride, occurs leading to erythro-1,5-hexadien-3-ols as the major or only product.

Claisen Orthoester Rearrangement Reaction with Secondary and Tertiary Allylic Alcohols: Synthesis of 1,2-Secochrysanthemates and their Structural Analogues

A simple route is described for the synthesis of 1,2 Seco-chrysanthemic acid and their structural analogues, employing Claisen orthoester rearrangement reaction in the key-step of synthesis.These acids have been prepared with a view to evaluating some of

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.

Cross-Condensation Reactions of Cycloalkanones with Aldehydes and Primary Alcohols under the Influence of Zirconocene Complexes.

Under the influence of zirconocene complex,Cp2ZrH2 (1) or Cp2Zr(O-i-Pr)2 (9),cycloalkanones 2 condensed directly with aliphatic aldehydes 3 or primary alcohols 7 to form 2-alkylidenecycloalkanones 4 or 2-alkyl-2-cycloalken-1-ones 8,respectively,in fair to substantial yields.The selectivity of the cross-condensations was slighty improved by using 1 in combination with a metal salt such as NiCl2.Dihydrojasmone (13) was synthesized in 35percent yield by one-step reaction from the commercially available 3-methylpentanone (2e) with pentanol (7b) in the presence of 1 and NiCl2.

Alkyl-substituted spiroundecenone derivatives, organoleptic utility thereof and processes for preparing same

Described are alkyl-substituted spiroundecenone derivatives defined according to the structure: STR1 wherein R1 represents isopropyl or hydrogen; R2, R3 and R4 are the same and each represents methyl or hydrogen; with the provisos that: (i) when R1 is isopropyl, R2, R3 and R4 are hydrogen; and (ii) when R2, R3 and R4 are each methyl, R1 is hydrogen, and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alkyl-substituted spiroundecenone derivatives.