54884-55-8Relevant articles and documents
Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes
Li, Feng,Zhou, Yirong,Yang, Heng,Wang, Ziqi,Yu, Qinqin,Zhang, Fang-Lin
supporting information, p. 3692 - 3695 (2019/05/24)
We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.
FXR receptor agonist
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, (2019/02/10)
The present invention discloses an FXR receptor agonist, belongs to the technical field of medicine, and particularly relates to a compound represented by a formula (I), a pharmaceutically acceptablesalt, an ester or a stereoisomer thereof, wherein R, R, R, M, L, L1, W, A , B, Q, m and n are defined in the specification. The present invention further relates to a preparation method of the compound, a pharmaceutical preparation, and applications in preparation of drugs for treatment and/or prevention of nonalcoholic fatty liver disease, primary biliary cirrhosis, lipid metabolism disorder, diabetic complication, malignant tumors and other related diseases mediated by FXR receptors. The formula I is defined in the specification.
Volatiles from the xylarialean fungus Hypoxylon invadens
Dickschat, Jeroen S.,Wang, Tao,Stadler, Marc
, p. 734 - 746 (2018/04/16)
The volatiles emitted by agar plate cultures of the xylarialean fungus Hypoxylon invadens were investigated by use of a closed loop stripping apparatus in combination with GC-MS. Several aromatic compounds were found that could only be identified by comparison to all possible constitutional isomers with different ring substitution patterns. For the set of identified compounds a plausible biosynthetic scheme was suggested that gives further support for the assigned structures.
Synthesis of oxygenated orthomethylbenzaldehydes via aryne [2+2] cycloaddition and benzocyclobutenol ring opening
Maturi, Mark M.,Ohmori, Ken,Suzuki, Keisuke
, p. 870 - 873 (2019/01/21)
Herein, a two-step procedure for the preparation of oxygenated ortho-methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core via benzyne [2+2] cycloadditions with acetaldehyde lithium enolate to give the corresponding benzocyclobutenols in high yields. Bond-selective ring opening of the benzocyclobutenols under basic conditions in methanol delivers the title compounds.
Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes
Xiao, Peihong,Tang, Zhixing,Wang, Kai,Chen, Hua,Guo, Qianyou,Chu, Yang,Gao, Lu,Song, Zhenlei
, p. 1687 - 1700 (2018/02/23)
A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.
The Key Role of the Nonchelating Conformation of the Benzylidene Ligand on the Formation and Initiation of Hoveyda-Grubbs Metathesis Catalysts
Bieszczad, Bartosz,Barbasiewicz, Micha?
, p. 10322 - 10325 (2015/07/07)
Experimental studies of Hoveyda-Grubbs metathesis catalysts reveal important consequences of substitution at the 6-position of the chelating benzylidene ligand. The structural modification varies conformational preferences of the ligand that affects its exchange due to the interaction of the coordinating site with the ruthenium center. As a consequence, when typical S-chelated systems are formed as kinetic trans-Cl2 products, for 6-substituted benzylidenes the preference is altered toward direct formation of thermodynamic cis-Cl2 isomers. Activity data and reactions with tricyclohexylphosphine (PCy3) support also a similar scenario for O-chelated complexes, which display fast trans-Cl2?cis-Cl2 equilibrium observed by NMR EXSY studies. The presented conformational model reveals that catalysts, which cannot adopt the optimal nonchelating conformation of benzylidene ligand, initiate through a high-energy associative mechanism.
2-BENZYL-BENZIMIDAZOLE COMPLEMENT FACTOR B INHIBITORS AND USES THEREOF
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Page/Page column 48, (2015/05/19)
The present invention provides a compound of formula (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical comp
Synthesis of (+)-varitriol analogues via novel and versatile building blocks based on julia olefination
Senthilmnrugan, Annamalai,Aidhen, Indrapal Singh
scheme or table, p. 555 - 564 (2010/04/24)
The synthesis of (+)-varitriol (1) analogues was achieved through, the use of Julia olefination. The potential anticancer properties of 1 coupled with, our interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of our research project. Efforts are aimed at the synthesis of building blocks 2 and 3 and to explore their use towards the synthesis of (+)-varit:riol analogues. Herein, we would, like to present the synthesis of building block 3 and its ability to react with variety of substituted aromatic-, heterocyclic- and carbohydrate-derived aldehydes to yield alkene 6 in moderate to good yields with E as the major isomer. The successful, coupling of 2 with (furanoside moieties) aldehydes 5k, 5m and 5n in particular and the obtainment of compound 23 reflect the promise associated with the new strategy.
Expeditious synthesis of benzopyrans via lewis acid-catalyzed C-H functionalization: Remarkable enhancement of reactivity by an ortho substituent
Mori, Keiji,Kawasaki, Taro,Sueoka, Shosaku,Akiyama, Takahiko
supporting information; experimental part, p. 1732 - 1735 (2010/09/05)
An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.
Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
Mandal, Samir Kumar,Roy, Subhas Chandra
experimental part, p. 11050 - 11057 (2009/04/11)
A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
