69824-91-5

Upstream product

• 930-68-7 cyclohexenone 
• 927-77-5 n-propylmagnesium bromide 
• 110-91-8 morpholine 
• 540-54-5 1-Chloropropane 
• 106-94-5 propyl bromide 
• 134654-92-5 3-(3-Iodopropyl)cyclohexan-1-one 
• 107-08-4 1-iodo-propane 
• 10557-57-0 propylmagnesium iodide 
• 63050-85-1 (+)-3-(3-Brompropyl)-cyclohexanon 
• 20498-05-9 3-allylcyclohexanone 
• 23074-59-1 3-isobutoxycyclohex-2-en-1-one 
• 6328-24-1 3-propyl-2-cyclohexen-1-one 
• 2417-93-8 propyllithium 

Downstream Products

• 1252759-79-7 C₂₆H₃₆N₂O 
• 73959-35-0 (R)-(+)-3-Propylcyclohexanone 

Relevant academic research and scientific papers

Pichia stipitis OYE 2.6 variants with improved catalytic efficiencies from site-saturation mutagenesis libraries

An earlier directed evolution project using alkene reductase OYE 2.6 from Pichia stipitis yielded 13 active site variants with improved properties toward three homologous Baylis-Hillman adducts. Here, we probed the generality of these improvements by testing the wild-type and all 13 variants against a panel of 16 structurally-diverse electron-deficient alkenes. Several substrates were sterically demanding, and as hoped, creating additional active site volume yielded better conversions for these alkenes. The most impressive improvement was found for 2-butylidenecyclohexanone. The wild-type provided less than 20% conversion after 24 h; a triple mutant afforded more than 60% conversion in the same time period. Moreover, even wild-type OYE 2.6 can reduce cyclohexenones with very bulky 4-substituents efficiently.

Assessing the Substrate Selectivities and Enantioselectivities of Eight Novel Baeyer-Villiger Monooxygenases toward Alkyl-Substituted Cyclohexanones

Genes encoding eight Baeyer-Villiger monooxygenases have recently been cloned from bacteria inhabiting a wastewater treatment plant. We have carried out a systematic investigation in which each newly cloned enzyme, as well as the cyclohexanone monooxygenase from Acinetobacter sp. NCIB 9871, was used to oxidize 15 different alkyl-substituted cyclohexanones. The panel of substrates included equal numbers of 2-, 3-, and 4-alkyl-substituted compounds to probe each enzyme's stereoselectivity toward a homologous series of synthetically important compounds. For all 4-alkyl-substituted cyclohexanones tested, enzymes were discovered that afforded each of the corresponding (S)-lactones in ≥98% ee. This was also true for the 2-alkyl-substituted cyclohexanones examined. The situation was more complex for 3-akyl-substituted cyclohexanones. In a few cases, single Baeyer-Villiger monooxygenases possessed both high regio- and enantioselectivities toward these compounds. More commonly, however, they showed only one type of selectivity. Nonetheless, enzymes with such properties might be useful as parts of a two-step bioprocess where an initial kinetic resolution is followed by a regioselective oxidation on the isolated, optically pure ketone.

Synthesis and structure-affinity relationships of 1,3,5-alkylsubstituted cyclohexylamines binding at NMDA receptor PCP site

A series of 1,3,5-alkylsubstituted cyclohexylamines 2 were synthesized as ligands for the N-methyl-D-aspartate (NMDA) receptor phencyclidine (PCP) binding site. Pure diastereomers with defined configuration of amino group 2- ax and 2-eq were obtained. The optimal size of 1,3,5-substituents was determined for cyclohexylamines 2 with an equatorial amino group in the lowest energy conformation using Hansch analysis. According to the data, the lipophilic part of cyclohexylamines 2 does not discriminate between hydrophobic regions of the PCP binding site but rather recognizes this site as a whole lipophilic pocket. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Radical cyclizations of 2-(ω-haloalkylthio)enones to thiapolycycloalkanones

Radical cyclization of 2-(ω-haloalkylthio)enones gives predominantly fused-thiapolycycloalkanones. (C) 2000 Elsevier Science Ltd.

3-Metallated enamines XI. Transmetallation of 3-Stannylated enamines - A new method to generate 1-aminoallyllithium compounds

The transmetallation of 3-stannylated enamines, 1-morpholino-3-(trialkylstannyl)cycloalk-1-enes and 3-morpholino-5-(tributylstannyl)hex-3-ene, with butyllithium is a new and general way to generate s1-aminoallyllithium compounds. Stabilization by aromatic substituents is not further necessarily as in the case of preparation by deprotonation and even the thermodynamically less stable exoamino derivatives are accessible. Therefore homoenolate-equivalents of cyclic ketones are made available. Thus, the corresponding 3-alkylated or 3-silylated cycloalkanones and alken-3-ones were prepared via the 1-morpholinoallyllithium compounds.

A Facile Synthesis of Bicycloalkan-1-ols. Evidence for Organosamarium Intermediates in the Samarium(II) Iodide Promoted Intramolecular Barbier-Type Reaction

Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicycloalkan-1-ols.Thus, a variety of 3-(ω-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic q

THE PREPARATION OF LITHIUM ORGANOCUPRATES FROM VARIOUS Cu(I) SALTS

Various Cu(I) salts have been tested as precursors for organocuprates in side-by-side comparisons under controlled conditions.CuCN and CuBr*SMe2 appear to be superior to CuI, CuBr, and CuCl.CuSCN and CuOTf are also good precursors in some circumstances.