15763-62-9

Upstream product

• 7080-86-6 1-(tert-butyl)-4-bromocyclohexane 
• 122-51-0 orthoformic acid triethyl ester 
• 7787-78-2 6-tert-Butyl-1-oxa-spiro[2.5]octane 
• 18881-26-0 (3r,6r)-6-(tert-butyl)-1-oxaspiro[2.5]octane 
• 201230-82-2 carbon monoxide 
• 2228-98-0 4-tert-butylcylohexene 
• 10601-39-5 trans-(4-tert-butyl-cyclohexyl)-methanol 
• 20451-50-7 cis-4-tert-butylcyclohexylcarbonyl chloride 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 13294-73-0 1-tert-butyl-4-methylenecyclohexane 
• 5451-55-8 4-tert-butylcyclohexanecarboxylic acid 
• 943-29-3 trans-4-(tert-butyl)cyclohexane-1-carboxylic acid 

Downstream Products

• 1083335-55-0 C₂₀H₃₀O 
• 1599472-37-3 (Z)-1-(4-t-butyl-1-cyclohexyl)-1,3-butadiene 
• 1599472-34-0 (E)-1-(4-t-butyl-1-cyclohexyl)-1,3-butadiene 

Relevant academic research and scientific papers

Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for cholesterol ester hydrolase

Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of α-difluoro-β-trifluoroketo-(5,10,15) and of α-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates.

Methylene C(sp3)-H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand

A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.

Palladium-catalyzed reduction of carboxylic acids to aldehydes with hydrosilanes in the presence of pivalic anhydride

A palladium catalyst system that allows the reduction of carboxylic acids to the corresponding aldehydes with hydrosilanes as reducing agent and pivalic anhydride as an indispensable reagent has been developed. A simple mixture of commercially available bis(dibenzylideneacetone)palladium(0) [Pd(dba) 2], tri(para-tolyl)phosphane and methylphenylsilane realized the reduction of various aliphatic carboxylic acids as well as benzoic acids to aldehydes in good to high yields. Copyright

Modified McFadyen-Stevens reaction for a versatile synthesis of aliphatic/aromatic aldehydes: Design, optimization, and mechanistic investigations

The traditional McFadyen-Stevens reaction requires harsh alkaline reaction conditions, thus precluding application to the synthesis of aliphatic aldehydes. Our modified McFadyen-Stevens reaction enables the transformation from the N,N-acylsulfonyl hydrazine to the corresponding aldehyde upon treatment with an imidazole-TMS imidazole combination without relying on oxidative or reductive reagents. The reduced basicity and in situ protection of the resulting aldehyde widens the substrate scope to include aliphatic aldehydes, even ones bearing an α-hydrogen atom. Close examination of the side reactions for particular substrates in combination with theoretical considerations via DFT calculations led to a mechanistic understanding of the McFadyen-Stevens reaction involving an acyl diazene and a hydroxy carbene as reasonable intermediates.

Stereoselective synthesis of cyclopropanes based on a 1,2-chirality transfer

A stereoselective route to enantiomerically enriched bicyclic cyclopropane derivatives 13 is described which is based on a conceptually novel 1,2-chirality transfer approach. The hyperconjugative interaction of an electronically excited carbonyl group with the σ* orbital of an adjacent C-X bond in the transition state of a hydrogen abstraction causes the preference of a certain conformation and consequently the differentiation between two diastereotopic methylene groups. The 1,2-chirality transfer is completed by a subsequent HX elimination which destroys the only stereogenic center in the reactants 12. Furthermore, it was found that contrary enthalpic and entropic influences result in the existence of an inversion temperature T0. Upon crossing T0 the stereoselectivity is reversed. Considering this temperature dependency, chirality transfer efficiencies of up to 83% could be achieved. The absolute configuration of most products could be unambiguously determined by VCD spectroscopy combined with DFT calculations.

Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study

(Chemical Equation Presented) Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals gave distinct EPR spectra thanks to surprisingly large β-hydrogen atom hyperfine splittings that enabled them to be characterized and monitored. DFT computations indicated that the axial species (X = CH2) had a higher barrier to rotation about the (O)Cα-Cα bond. The computed difference ΔH° for the axial and equatorial radicals (R = H, X = CH2) was 0.8 kcal mol -1.

Photochemical synthesis of highly functionalized cyclopropyl ketones

A series of di- and trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3. The irradiation of 3 and 5 must be performed in the presence of an acid scavenger (1-methyl-1H-imidazole) to obtain the cyclopropanes 11 in good yields. The synthetic efficiency of the method was, among other things, demonstrated by the preparation of a highly strained bicyclo[2.1.0]pentane 11i in good yield. The mechanism of the photochemical cyclization was investigated by means of photokinetic measurements, as well as by quantum-chemical calculations. It was shown that the presence of the leaving group substantially influences all steps of the photochemical reaction cascade. The X-ray crystal structures of 11j and exo-11k were also determined.

Rearrangements of substituted 3-aza-1,2,5-hexatrienes. 3. The scope and versatility of an extremely mild 3-aza-Cope reaction

An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily av

CCK ANALOGS WITH APPETITE REGULATING ACTIVITY

The invention is directed to novel CCK analogs wherein Tryptophan and/or Phenylalamine are substituted with a radical which provides enhanced appetite suppressant activity to the peptide.

THE STEREOCHEMISTRY OF METAL CATALYSED HYDROGEN CYANIDE ADDITION TO ALKENES

Reaction of both terminal and cyclic alkenes have been shown to occur in a stereospecifically cis-manner with deuterium cyanide when a catalyst system based on Pd(DIOP)2 was used.Reactions of cyclohexene give only the products of equatorial cyanide incorporation.