3395-91-3Relevant articles and documents
Synthesis of β-haloketones by β-addition reactions of α,β-unsaturated ketones with BX3 (X = Br, Cl) as halide source
Lee, Adam Shih-Yuan,Wang, Shu-Huei,Chang, Yu-Ting
, p. 364 - 368 (2014)
A series of β-bromoketones and β-chloroketones were synthesized by the addition reactions of α,β-unsaturated ketones under BX 3 (X = Br, Cl) and ethylene glycol reaction system. The α,β-unsaturated ester also was successfully converted to its corresponding β-bromoester under the reaction condition. A series of β-bromoketones and β-chloroketones were synthesized by the addition reactions of α,β-unsaturated ketones under BX3 (X=Br, Cl) and ethylene glycol reaction system. Copyright
Preparation method of 3-bromopropionate compound
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Paragraph 0026, (2020/06/30)
The invention relates to the field of organic synthesis, and discloses a preparation method of a 3-bromopropionate compound. The method comprises the following steps: reacting acetyl bromide used as araw material with an alcohol solvent to generate hydrogen bromide in situ, and carrying out a 1,4-addition reaction on the hydrogen bromide and an acrylate compound to obtain the 3-bromopropionate compound. According to the invention, the preparation method disclosed by the invention belongs to a one-pot method in chemistry and has few steps; by-products of acetate and alcohol solvents can be rectified and recycled, so that less three wastes are generated; and more importantly, the boiling points of the product acetate and the product 3-bromopropionate compound generated by the reaction haveobvious difference, so that distillation or rectification separation is facilitated after the reaction is finished.
Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds
Zhu, Ru-Yi,Saint-Denis, Tyler G.,Shao, Ying,He, Jian,Sieber, Joshua D.,Senanayake, Chris H.,Yu, Jin-Quan
supporting information, p. 5724 - 5727 (2017/05/04)
We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands.
Peptide ligation assisted by an auxiliary attached to amidyl nitrogen
Li, Juan,Cui, Hong-Kui,Liu, Lei
scheme or table, p. 1793 - 1796 (2010/06/13)
New thiol-containing auxiliaries were developed for peptide ligation. They were placed at the amidyl N-atom in the second amino acid residue of a peptide fragment. With the new auxiliaries, peptide ligation could be conducted at non-Cys and non-Gly sites. Compared to other recently developed auxiliaries, an important feature of the present design was that the new auxiliaries were generally applicable and readily removable.
Synthesis of [3-13C]-, [4-13C]- and [11- 13C]-porphobilinogen
Dawadi, Prativa B. S.,Schulten, Els A. M.,Lugtenburg, Johan
experimental part, p. 341 - 349 (2011/07/08)
[4-13C]-porphobilinogen 1a, [3-13C]-porphobilinogen 1b and [11-13C]-porphobilinogen 1c are prepared from [1- 13C]-3-(tetrahydropyran-20-yloxy)-propionaldehyde 2a, methyl [4- 13C]-4-nitrobutyrate 3b and [1-13C]-isocyanoacetonitrile 5c, respectively. The building blocks 2, 3 and 5 can be prepared efficiently in any isotopomeric form. Via base-catalyzed condensation of these building blocks porphobilinogen can be enriched with 13C and 15N stable isotopes at any position and combination of positions. Copyright
Rotamers of palladium complexes bearing IR active N-heterocyclic carbene ligands: Synthesis, structural characterization and catalytic activities
Huynh, Han Vinh,Wu, Jiang
supporting information; experimental part, p. 323 - 331 (2009/04/13)
The preparation and properties of mono- versus bis(carbene) Pd(II) complexes bearing unsymmetrical cyano- and ester-functionalized NHC ligands as potential IR probes were studied in detail. Direct reaction of Pd(OAc)2 with functionalized imidazolium salts afforded either bis(carbene) (3a, c) or monocarbene complexes (5, 6) with a N-coordinated imidazole co-ligand. The latter were exclusively obtained with N-ethylene substituted salts, which were found to undergo N-C cleavage reaction. The milder Ag-carbene transfer reaction on the other hand was tolerable to the length of the substituents and the nature of the functional groups. All bis(carbene) complexes (3a-c, 4a-c) were obtained as a inseparable mixture of square-planar trans-anti and trans-syn rotamers. The identity, ratio and dynamic equilibrium of these rotamers have been investigated and the relatively high rotational barrier for rotamers of 3a was estimated to be about 74 kJ mol-1 at 380 K. All eight complexes were fully characterized by NMR and IR spectroscopies, ESI mass spectrometry and X-ray single crystal and powder diffraction. A preliminary catalytic study showed that ester-functionalized complexes 4a and 4b gave rise to highly active catalyst in the double Mizoroki-Heck coupling of aryl dibromides, while the in situ ester-hydrolyzed complexes were also active in the coupling of activated aryl chlorides.
1H-PYRAZOLE AND 1H-PYRROLE-AZABICYCLIC COMPOUNDS WITH ALFA-7 NACHR ACTIVITY
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Page 76, (2010/02/06)
The invention provides compounds of Formula (I), wherein Azabicyclo is Formula (I, II, III, IV, V, VI, VII); W is Formula (m); where the variables have the definitions discussed herein. These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals to treat a disease or condition in which α7 is known to be involved.
Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones
Wolfe, Saul,Wilson, Marie-Claire,Cheng, Ming-Huei,Shustov, Gennady V.,Akuche, Christiana I.
, p. 937 - 960 (2007/10/03)
Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.
A selective method for the preparation of aliphatic methyl esters in the presence of aromatic carboxylic acids
Rodriguez,Nomen,Spur,Godfroid
, p. 8563 - 8566 (2007/10/03)
2,2-Dimethoxypropane, methanol and a catalytic amount of HCl selectively esterify aliphatic carboxylic acids, in the presence of aromatic carboxylic acids, at room temperature and in high yields.
A New Oxaanalog of Myristic Acid that Suppresses Replication of Human Immunodeficiency Virus
Vodovozova, E. L.,Mikhalev, I. I.,Rzhaninova, A. A.,Garaev, M. M.,Molotkovsky, Yul. G.
, p. 626 - 632 (2007/10/03)
A series of oxaanalogs of myristic acid were synthesized and tested for antiviral activity in MT4 cells infected with human immunodeficiency virus 1 (HIV-1).The synthesized acids have no toxic effect on uninfected MT4 cells at a concentration of 100μM. 14,14,14-Trifluoro-12-oxatetradecanoic acid substantially (by 75percent) inhibits the reproduction of HIV-1.Other compounds synthesized, (7Z)-13-, (9Z)-13-, and (7Z)-11-oxatetradecenoic acids, exhibit no antiviral effect.Key words: inhibitors of retroviruses; anti-HIV agents; protein N-myristoylation; mystoylCoA: protein-N-myristoyltransferase; myristic acid; oxaanalogs; inhibitors of virus-specific protein myristoylation
