36291-48-2Relevant academic research and scientific papers
Synthesis, identification and application of aldehyde reactive dyes
Chen, Xiao,Ding, Keyi,Jun, Liu
, p. 404 - 412 (2015)
Nine aldehyde reactive dyes, designated D1- D9, were synthesized. Among them, D1 and D2 were synthesized by "grafting" alizarin red and alizarin yellow GG, respectively, to the α-C of n-butyl-aldehyde; D3 and D4 were synthesized by "grafting" alizarin red and alizarin yellow GG, respectively, to the methyl-C of 4-methyl-cinnamaldehyde; D5- D9 were synthesized by "grafting" alizarin red, alizarin yellow GG or self-prepared colorants to the α-C of glutaraldehyde. UV-Vis, FTIR, ESI-MS, elemental analysis and 1H NMR were applied to identify the target products. Aluminum-tanned wet-white sheep leather was chosen as substrate for the application experiments, and their four dyeing property indexes, i.e., substantivity (S), exhaustion (E), fixation (F) and reactivity (R) were measured. The results indicated that, without adding of neutral salts and under mild conditions (T = 35-45 °C, pH = 4.0-6.5), all these dyes could dye wet-white leather within 1.5 h, and the dyed leather possessed a satisfactory washing-fastness.
Chain Walking as a Strategy for Carbon-Carbon Bond Formation at Unreactive Sites in Organic Synthesis: Catalytic Cycloisomerization of Various 1,n-Dienes
Hamasaki, Taro,Aoyama, Yuka,Kawasaki, Junichi,Kakiuchi, Fumitoshi,Kochi, Takuya
, p. 16163 - 16171 (2015)
Carbon-carbon bond formation at unreactive sp3-carbons in small organic molecules via chain walking was achieved for the palladium-catalyzed cycloisomerization of 1,n-dienes. Various 1,n-dienes (n = 7-14) such as those containing cyclic alkenes, acyclic internal alkenes, and a trisubstituted alkene can be used for the chain-walking cycloisomerization/hydrogenation process, and five-membered ring compounds including simple cyclopentane and pyrrolidine derivatives can easily be prepared. Chain walking over a tertiary carbon was also found to be possible in the cycloisomerization. It is not necessary for the linker portion of the diene to contain a quaternary center, and diene substrates with two alkene moieties linked by a tertiary carbon or a nitrogen atom can also be used as substrates. Column chromatography using silica gel containing silver nitrate was found to be effective for isolating some of the cycloisomerization products without hydrogenation. Deuterium-labeling experiments provided direct evidence to show that the reaction proceeds via a chain-walking mechanism.
Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas
Tait, Michael B.,Ottersbach, Philipp A.,Tetlow, Daniel J.,Clayden, Jonathan
, p. 1245 - 1252 (2014)
The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.
N-(4-Methoxyphenyl)-substituted bicyclic isothioureas: effect on morphology of cancer cells
Alexeev, Alexander A.,Evdokimova, Anna V.,Kuznetsov, Sergei A.,Milaeva, Elena R.,Nurieva, Evgeniya V.,Zefirova, Olga N.
, p. 288 - 290 (2021/06/07)
Bicyclic isothioureas of N-(4-methoxyphenyl)-2-aminocycloalkane[d]thiazole type were obtained using intramolecular electrophilic cyclization of N-(cycloalk-2-enyl)-N′-(4-methoxyphenyl)thioureas. Isothiourea fused with sevenmembered ring caused noticeable
Catalytic Living Ring Opening Metathesis Polymerisation: The Importance of Ring Strain in Chain Transfer Agents
Liu, Peng,Yasir, Mohammad,Kilbinger, Andreas F. M.
supporting information, p. 15278 - 15282 (2019/09/17)
A recently developed catalytic living ring opening metathesis polymerisation (ROMP) was investigated using a series of reversible chain transfer agents (CTA) carrying either cyclopentene or cyclohexene rings, differing only in ring strain. All cyclopentene derivatives examined showed significantly faster reaction rates than the corresponding cyclohexene derivatives. This resulted in lower molecular weight dispersities and better control of the molecular weight for the cyclopentene compared to the cyclohexene CTAs. Both Grubbs’ second and third generation catalysts could be employed in catalytic living ROMP using cyclopentene CTA derivatives. The kinetics of different CTAs were studied, block copolymers were synthesised and residual ruthenium quantified by ICP-OES. All polymers were fully characterised by NMR, GPC and MALDI-ToF mass spectrometry. The new cyclopentene CTAs are readily synthesised in a few straightforward steps and provide faster reaction kinetics than all previously reported reversible CTAs.
(Guanidine)copper Complex-Catalyzed Enantioselective Dynamic Kinetic Allylic Alkynylation under Biphasic Condition
Cui, Xi-Yang,Ge, Yicen,Tan, Siu Min,Jiang, Huan,Tan, Davin,Lu, Yunpeng,Lee, Richmond,Tan, Choon-Hong
supporting information, p. 8448 - 8455 (2018/06/22)
Highly enantioselective allylic alkynylation of racemic bromides under biphasic condition is furnished in this report. This approach employs functionalized terminal alkynes as pro-nucleophiles and provides 6- and 7-membered cyclic 1,4-enynes with high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. Enantioretentive derivatizations highlight the synthetic utility of this transformation. Cold-spray ionization mass spectrometry (CSI-MS) and X-ray crystallography were used to identify some catalytic intermediates, which include guanidinium cuprate ion pairs and a copper-alkynide complex. A linear correlation between the enantiopurity of the catalyst and reaction product indicates the presence of a copper complex bearing a single guanidine ligand at the enantio-determining step. Further experimental and computational studies supported that the alkynylation of allylic bromide underwent an anti-SN2′ pathway catalyzed by nucleophilic cuprate species. Moreover, metal-assisted racemization of allylic bromide allowed the reaction to proceed in a dynamic kinetic fashion to afford the major enantiomer in high yield.
Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes
Maeda, Hajime,Uesugi, Tomoya,Fujimoto, Yasufumi,Mukae, Hirofumi,Mizuno, Kazuhiko
, p. 198 - 206 (2017/02/10)
Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.
Inhibitory Kappa B Kinase α (IKKα) Inhibitors That Recapitulate Their Selectivity in Cells against Isoform-Related Biomarkers
Anthony, Nahoum G.,Baiget, Jessica,Berretta, Giacomo,Boyd, Marie,Breen, David,Edwards, Joanne,Gamble, Carly,Gray, Alexander I.,Harvey, Alan L.,Hatziieremia, Sophia,Ho, Ka Ho,Huggan, Judith K.,Lang, Stuart,Llona-Minguez, Sabin,Luo, Jia Lin,McIntosh, Kathryn,Paul, Andrew,Plevin, Robin J.,Robertson, Murray N.,Scott, Rebecca,Suckling, Colin J.,Sutcliffe, Oliver B.,Young, Louise C.,Mackay, Simon P.
, p. 7043 - 7066 (2017/09/07)
IKKβ plays a central role in the canonical NF-kB pathway, which has been extensively characterized. The role of IKKα in the noncanonical NF-kB pathway, and indeed in the canonical pathway as a complex with IKKβ, is less well understood. One major reason for this is the absence of chemical tools designed as selective inhibitors for IKKα over IKKβ. Herein, we report for the first time a series of novel, potent, and selective inhibitors of IKKα. We demonstrate effective target engagement and selectivity with IKKα in U2OS cells through inhibition of IKKα-driven p100 phosphorylation in the noncanonical NF-kB pathway without affecting IKKβ-dependent IKappa-Bα loss in the canonical pathway. These compounds represent the first chemical tools that can be used to further characterize the role of IKKα in cellular signaling, to dissect this from IKKβ and to validate it in its own right as a target in inflammatory diseases.
Step-Economical Photoassisted Diversity-Oriented Synthesis: Sustaining Cascade Photoreactions in Oxalyl Anilides to Access Complex Polyheterocyclic Molecular Architectures
Kuznetsov, Dmitry M.,Kutateladze, Andrei G.
supporting information, p. 16584 - 16590 (2017/11/28)
Atom- and step-economy in photoassisted diversity-oriented synthesis (DOS) is achieved with a versatile oxalyl linker offering rapid access to complex alkaloid mimics in very few experimentally simple steps: (i) it allows for fast tethering of the photoac
Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives
Maeda, Hajime,Wada, Hidenori,Mukae, Hirofumi,Mizuno, Kazuhiko
, p. 29 - 41 (2016/11/16)
Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.
