129518-99-6Relevant articles and documents
Iron-Catalyzed Intermolecular Functionalization of Non-Activated Aliphatic C?H Bonds via Carbene Transfer
Rodríguez, Mònica,Font, Gemma,Nadal-Moradell, Joel,Hernán-Gómez, Alberto,Costas, Miquel
supporting information, p. 5116 - 5123 (2020/10/06)
The modification of strong Csp3?H bonds via iron carbene intermediates under mild reaction conditions has been an important challenge with attractive prospective in organic synthesis. In this work, we show the efficient combination of an electrophilic iron catalyst with a lithium Lewis acid for the functionalization of strong Csp3?H bonds of cyclic and linear alkanes by the activation of commercially available ethyl diazoacetate (EDA). The reaction proceeds with good yields, under mild reaction conditions (40 °C) and large excess of substrate is not needed. In addition, excellent activity is observed in the cyclopropanation of challenging aliphatic olefins. (Figure presented.).
Synthesis and Biological Activity of New 4-tert-Butylcyclohexanone Derivatives
Kozio?, Agata,Jasnowski, Mateusz,Grela, Ewa,Szczepanik, Maryla,Gabry?, Beata,Dancewicz, Katarzyna,Lochyński, Stanis?aw
, (2019/01/25)
In the synthesis performed in this study, derivatives of 4-tert-butylcyclohexanone 1 were obtained using typical reactions of organic synthesis. The bioactivity of the selected compounds was evaluated. 1-(Bromomethyl)-8-tert-butyl-2-oxaspiro[4.5]decan-3-o
A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources
Lee, Sumin,Lei, Honghui,Rovis, Tomislav
supporting information, p. 12536 - 12540 (2019/08/26)
We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselect
Synthetic method for 4-tertiary butyl cyclohexaneacetic acid
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Paragraph 0022, (2016/10/10)
The invention provides a synthetic method for 4-tertiary butyl cyclohexaneacetic acid. The synthetic method comprises the steps of: firstly adding sodium hydride into dried tetrahydrofuran; stirring the mixture and reducing the temperature to 0 DEG C; adding triethyl phosphonoacetate and stirring the mixture; adding a tetrahydrofuran solution of 4-tertiary butyl cyclohexanone, and raising the temperature to room temperature and stirring the mixture; then adding obtained 4-tertiary butyl ethyl cyclohexylideneacetate into methanol; then adding raney nickel to react in a hydrogen atmosphere; and finally mixing the 4-tertiary butyl ethyl cyclohexylacetate with an aqueous solution of sodium hydroxide, and heating and stirring the mixture to obtain the 4-tertiary butyl cyclohexaneacetic acid. The method provides the effective method for producing the 4-tertiary butyl cyclohexaneacetic acid. The method is few in step, high in yield, simple in post-treatment such as purification and easy for industrial production and operation.
Construction of a quaternary carbon at the carbonyl carbon of the cyclohexane ring
Kaneko, Yuki,Kiyotsuka, Yohei,Acharya, Hukum P.,Kobayashi, Yuichi
supporting information; experimental part, p. 5482 - 5484 (2010/10/04)
High SN2′ selectivity in the allylic substitution of cyclohexylidene ethyl picolinates with copper reagents prepared from RMgBr and CuBr·Me2S was realized by addition of ZnX2 (X = I, Br, Cl). Furthermore, ZnX2 accelerated the reaction with the bulky iPr reagent. The Royal Society of Chemistry 2010.
Microwave-assisted regioselective olefinations of cyclic mono- and di-ketones with a stabilized phosphorus ylide
Wu, Jinlong,Li, Dan,Wu, Huafeng,Sun, Lijie,Dai, Wei-Min
, p. 4643 - 4650 (2007/10/03)
A number of cyclic mono- and di-ketones underwent regioselective olefination with (carbethoxyethylidene)triphenylphospharane under controlled microwave heating. The Wittig reaction of 4-substituted cyclohexanones or 1,2- and 1,4-cyclohexanediones with the ylide at 190 °C for 20 min in MeCN afforded the exocyclic olefins in >94:6 isomer ratios. On the other hand, the same reactions carried out at 230 °C for 20 min in the presence of 20 mol % DBU furnished the endocyclic olefins in >83:17 isomer ratios. The base-mediated isomerization of the exocyclic olefins into the endocyclic isomers was primarily driven by thermodynamic stability of the products and the effect of ring structures on deconjugation was examined.
Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement
Engel, Douglas A.,Dudley, Gregory B.
, p. 4027 - 4029 (2007/10/03)
An atom-economical and efficient olefination strategy for ketones is described. Ethoxyacetylide addition followed by a gold-catalyzed Meyer-Schuster rearrangement affords α,β-unsaturated esters, generally in excellent overall yield from the starting ketones. The alkynophilicity of Au3+ promotes an interaction with the electron-rich acetylenes that catalyzes the Meyer-Schuster rearrangement selectively over other conceivable pathways.
Highly regioselective Wittig reactions of cyclic ketones with a stabilized phosphorus ylide under controlled microwave heating
Wu, Jinlong,Wu, Huafeng,Wei, Shaoyong,Dai, Wei-Min
, p. 4401 - 4404 (2007/10/03)
Significant base and temperature effects on the Wittig reactions of cyclohexanones with (carbethoxymethylene)triphenylphosphorane under microwave irradiation were observed. For the Wittig reactions carried out in a domestic microwave oven under solvent-free conditions, the initially formed exo-olefin products isomerized into the thermodynamically more stable endo-olefins due to uncontrolled high reaction temperature. In sharp contrast, under controlled microwave heating, both exo- and endo-olefins have been selectively synthesized by accurately regulating the reaction temperature with or without a base.
Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization
Ferraz, Helena M. C.,Longo Jr., Luiz S.,Zukerman-Schpector, Julio
, p. 3518 - 3521 (2007/10/03)
The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.
Thioepoxide formation by ring closure of allylthiyl radicals - A novel rearrangement of allylic thionitrites
Cavero, Marta,Motherwell, William B.,Potier, Pierre,Weibel, Jean-Marc
, p. 2394 - 2395 (2007/10/03)
Tertiary allylic thionitrites undergo thermal rearrangement to α,β-episulfide nitroso dimers via ring closure of allylthiyl radicals.
