173542-65-9Relevant academic research and scientific papers
Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization
Li, Hengchao,Chen, Hang,Zhou, Yang,Huang, Jin,Yi, Jundan,Zhao, Hongcai,Wang, Wei,Jing, Linhai
, p. 555 - 559 (2020/02/05)
A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.
Cobalt-catalyzed (Z)-selective semihydrogenation of alkynes with molecular hydrogen
Chen, Caiyou,Huang, Yi,Zhang, Zongpeng,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 4612 - 4615 (2017/04/28)
Cobalt-catalyzed highly (Z)-selective semihydrogenation of alkynes using molecular H2 was developed using commercially available and cheap cobalt precursors. A variety of (Z)-alkenes were obtained in moderate to excellent selectivities [(Z)-alkene/(E)-alkene/alkane ratio up to >99 : 1 : 1] and it was found that the readily available ethylenediamine ligand is crucial in determining the selectivity.
Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes
Jirásek, Michael,Straková, Karolína,Nevesely, Tomá?,Svobodová, Eva,Rottnerová, Zdeňka,Cibulka, Radek
, p. 2139 - 2146 (2017/04/24)
The [2+2] photocycloaddition mediated by 1-butyl-3-methyl-7,8-dimethoxyalloxazine (1) has been found to be an effective tool for cyclising ω-phenyl- and ω,ω′-diphenyl-4-aza-1,6-heptadienes, in which the nitrogen atom is protected by acylation or quaternisation, towards the synthesis of a variety of phenyl- and diphenyl-3-azabicyclo[3.2.0]heptanes and their corresponding quaternary salts. Thia derivatives, with the sulfur atom in the form of a sulfone group, underwent an analogous cyclisation. Advantageously, visible light (400 nm) was used for the cycloadditions in the presence of 1, in contrast to the previously described procedures affording azabicyclo[3.2.0]heptanes by using UV irradiation. Practical applications are demonstrated through the synthesis of bicyclic quaternary ammonium salts, 6-phenyl-azabicyclo[3.2.0]heptanes known to exhibit biological activity or chiral spiro ammonium salts. Flavin 1 was also found to promote the efficient E→Z isomerisation of electron-rich cinnamyl derivatives to produce mixtures enriched with the Z isomer (with Z/E ratios of up to 77:23).
Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
Soltanzadeh, Bardia,Jaganathan, Arvind,Staples, Richard J.,Borhan, Babak
supporting information, p. 9517 - 9522 (2015/08/11)
An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification. A highly regioselective intermolecular haloetherification that proceeds with excellent enantioselectivity, catalyzed by cinchona alkaloid dimers, is reported. The regioselectivity is preserved for unbiased alkyl substituted allyl amides with either E or Z geometry. (DHQD)2PHAL=hydroquinidine 1,4-phthalazinediyl diether.
Tailoring flavins for visible light photocatalysis: organocatalytic [2+2] cycloadditions mediated by a flavin derivative and visible light
Mojr, Viktor,Svobodová, Eva,Straková, Karolína,Nevesely, Tomá?,Chudoba, Josef,Dvo?áková, Hana,Cibulka, Radek
, p. 12036 - 12039 (2015/07/28)
A new application of flavin derivatives in visible light photocatalysis was found. 1-Butyl-7,8-dimethoxy-3-methylalloxazine, when irradiated by visible light, was shown to allow an efficient cyclobutane ring formation via an intramolecular [2+2] cycloaddition of both styrene dienes, considered as electron-rich substrates, and electron-poor bis(arylenones), presumably proceeding via an energy transfer mechanism.
Synthesis, Biological Activity, and ADME Properties of Novel S-DABOs/N-DABOs as HIV Reverse Transcriptase Inhibitors
Radi, Marco,Pagano, Mafalda,Franchi, Luigi,Castagnolo, Daniele,Schenone, Silvia,Casaluce, Gianni,Zamperini, Claudio,Dreassi, Elena,Maga, Giovanni,Samuele, Alberta,Gonzalo, Encarna,Clotet, Bonaventura,Este, Jose A.,Botta, Maurizio
experimental part, p. 883 - 896 (2012/08/08)
Previous studies aimed at exploring the SAR of C2-functionalized S-DABOs demonstrated that the substituent at this position plays a key role in the inhibition of both wild-type RT and drug-resistant enzymes, particularly the K103N mutant form. The introdu
Direct palladium-catalyzed intermolecular allylation of highly electron-deficient polyfluoroarenes
Fan, Shilu,Chen, Fei,Zhang, Xingang
supporting information; experimental part, p. 5918 - 5923 (2011/08/02)
A simple operation: The use of readily available PPh3, high reaction efficiency, and good stereo- and regioselectivity provided useful and operationally simple access to polyfluoroarylated derivatives through the title transformation (see schem
Enantioselective synthesis of trans-aryl-and-heteroaryl-substituted cyclopropylboronates by copper (I)-catalyzed reactions of allylic phosphates with a diboron derivative
Zhong, Chongmin,Kunii, Shun,Kosaka, Yuki,Sawamura, Masaya,Ito, Hajime
supporting information; experimental part, p. 11440 - 11442 (2010/10/04)
A new asymmetric route for the synthesis of trans-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (Z)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (E)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed.
Design, synthesis, and evaluation of matrix metalloprotease inhibitors bearing cyclopropane-derived peptidomimetics as P1′ and P2′ replacements
Reichelt, Andreas,Gaul, Christoph,Frey, Robin R.,Kennedy, April,Martin, Stephen F.
, p. 4062 - 4075 (2007/10/03)
We have previously used trisubstituted cyclopropanes as peptide replacements to induce conformational constraints in known pseudopeptide inhibitors of a number of important enzymes. Cyclopropane-derived peptide mimics are novel in that they are among the few replacements that locally orient the peptide backbone and the amino acid side chain in a predefined manner. Although these dipeptide isosteres have been employed to orient amino acid side chains mimicking the gauche(-) conformation of χ1-space, their ability to project the side chains into an anti orientation has not been evaluated. As a first step toward this goal, the conformationally constrained pseudopeptides 8 and 10 and their corresponding flexible analogues 9 and 11 were prepared and tested as inhibitors of matrix metalloproteinases (MMPs). These compounds are analogues of 4 and 5, which were known to be potent MMP inhibitors. The anti orientations of the isopropyl side chain in 8 and the aromatic ring in 10 relative to the peptide backbone substituents on the cyclopropane were predicted to correspond to the known orientations of the P1′ and P2′ side chains of 5 when bound to MMPs. Hence, 8 and 10 were designed explicitly to probe topological features of the S1′ or the S2′ binding pockets of the MMPs. They were also designed to explore the importance of the P1′-P2′ amide group, which is known to form highly conserved hydrogen bonds in several MMP-inhibitor complexes, and the viability of introducing a retro amide linkage between P2′ and P3′. Pseudopeptides 8 and 9 were found to be weak competitive inhibitors of a series of MMPs. Any entropically favorable conformational constraints that were induced by the cyclopropane in 8 were thus overwhelmed by the loss of the hydrogen bonding capability associated with the P1′-P2′ amide group. On the other hand, compounds 10 and 11, which contain a P2′-P3′ retro amide group, were modest competitive inhibitors of a series of MMPs. The results obtained for 10 and 11 suggest that there may be a loss of hydrogen bonding capability associated with introducing the P2′-P3′ retro amide group. However, because the conformationally constrained pseudopeptide 10 was significantly more potent than its flexible analogue 11, trisubstituted cyclopropanes related to 3 may serve as useful rigid dipeptide replacements in some biologically active pseudopeptides.
3,3-Disubstituted allyl alcohols from palladium-catalyzed coupling of hydroaluminated propargyl alcohols with aryl iodides
Havranek, Miroslav,Dvorak, Dalimil
, p. 2125 - 2130 (2007/10/03)
3,3-Disubstituted prop-2-en-1-ols 4 were synthesized with a high degree of stereoselectivity from 3-substituted prop-2-yn-1-ols 1 via hydroalumination and subsequent Pd-catalyzed coupling with aryl iodides 3.
