599-91-7Relevant articles and documents
Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters
Wang, Yang,Deng, Lingling,Deng, Yu,Han, Jianlin
, p. 4674 - 4680 (2018/04/26)
A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the first time in the synthesis of sulfonic aliphatic esters. This multicomponent reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides a new and efficient strategy for the synthesis of sulfonic esters.
Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur
Iazykov, Mykyta,Canle, Moisés,Santaballa, J. Arturo,Rublova, Ludmila
, (2017/09/08)
We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.
New process for the production of alkyltosylate from alcohol and para-toluene sulfonic acid
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Paragraph 0026; 0027, (2016/12/16)
The present invention relates to a new method for producing an alkyltosylate derivative which plays an important role in transforming a hydroxy group of alcohol into other usage intermediate in a process of synthesizing core intermediates in a fine chemical field such as medicines, agricultural chemicals, dyes, electronic materials, etc. The present invention, as compared with previous technologies which has a long preprocess time for acquiring a catalyst to activate para-toluene sulfonic acid and needs an intense reaction condition in spite of using the catalyst, provides the new method for producing the alkyltosylate derivative having a characteristic of activating the para-toluene sulfonic acid under a warm condition equal to or lower than 25anddeg;C by making the para-toluene sulfonic acid react with the bis(trichloromethyl)carbonate, tribasic potassium phosphate and triethylamine with an amount of catalyst, and then making the para-toluene sulfonic acid react with alcohol, thereby contributing greatly to related industries such as dyes, agricultural chemicals, medicines, electronic materials, etc.COPYRIGHT KIPO 2015
Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions
Gao, Jian,Pan, Xiaojun,Liu, Juan,Lai, Junyi,Chang, Liming,Yuan, Gaoqing
, p. 27439 - 27442 (2015/03/31)
An iodine-induced synthesis of sulfonate esters via cross-coupling reactions of sodium sulfinates with phenols is reported. This synthetic route is low-cost, facile, green and efficient, and could afford the target products with good to excellent yields u
Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity
Timko, Luká?,Fischer-Fodor, Eva,Garajová, Mária,Mrva, Martin,Chereches, Gabriela,Ondriska, Franti?ek,Bukovsky, Marián,Luká?, Milo?,Karlovská, Janka,Kubincová, Janka,Devínsky, Ferdinand
, p. 263 - 273 (2015/05/26)
Twelve derivatives of hexadecylphosphocholine (miltefosine) were synthesized to determine how the position and length of the alkyl chain within the molecule influence their biological activities. The prepared alkylphosphocholines have the same molecular formula as miltefosine. Activity of the compounds was studied against a spectrum of tumour cells, two species of protozoans, bacteria and yeast. Antitumour efficacy of some alkylphosphocholines measured up on MCF-7, A2780, HUT-78 and THP-1 cell lines was higher than that of miltefosine. The compounds showed antiprotozoal activity against Acanthamoeba lugdunensis and Acanthamoeba quina. Some of them also possess fungicidal activity against Candida albicans equal to miltefosine. No antibacterial activity was observed against Staphylococcus aureus and Escherichia coli. A difference in position of a long hydrocarbon chain within the structure with maximum efficacy was observed for antitumour, antiprotozoal and antifungal activity.
SYNTHESIS OF CHIRALLY PURIFIED SUBSTITUTED BENZOTHIAZOLE DIAMINES
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Page/Page column 52, (2011/10/03)
Methods for preparing chirally purified substituted 4,5,6,7-tetrahydro-benzotiazole diamines such as, for example, (6R)2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole and purifying a dominant enantiomer of substituted 4,5,6,7-tetrahydro-benzotiazole diamines from entantiomerically enriched mixtures of substituted 4,5,6,7-tetrahydro-benzotiazole diamines are provided herein.
Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides
Yang, Chu-Ting,Zhang, Zhen-Qi,Liu, Yu-Chen,Liu, Lei
supporting information; experimental part, p. 3904 - 3907 (2011/05/15)
Non-activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper-catalyzed cross-coupling with aryl boron compounds and alkyl 9-BBN reagents (see scheme; 9-BBN=9-borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium- and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.
COMPOSITIONS AND METHODS OF USING (R)-PRAMIPEXOLE
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Page/Page column 101, (2010/04/03)
Pharmaceutical compositions of (R)-pramipexole and one or more secondary therapeutic agents such as, for example, dopamine agonists, dopaminergic agonists, COMT inhibitors, MOA inhibitors, excitatory amino acid antagonists, growth factors, neurotrophic factors, antioxidants, anti-inflammatory agents, immunomodulators, anti-glutamatergics, ion channel blockers, α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, heat shock protein inducers/ protein disaggregators and downregulators, monoamine oxidase type B (MOAB) inhibitors, multi-target agents, kinase inhibitors, Bcl inducers, histone deacetylase (HDAC) mediators, glial modulators, mitochondrial energy promoting agents, myostatin inhibitors, caspase inhibitors and combinations thereof or those related to mitochondrial dysfunction or increased oxidative stress are disclosed.
Design, synthesis, and structure-affinity relationships of regioisomeric N-benzyl alkyl ether piperazine derivatives as σ-1 receptor ligands
Moussa, Iman A.,Banister, Samuel D.,Beinat, Corinne,Giboureau, Nicolas,Reynolds, Aaron J.,Kassiou, Michael
experimental part, p. 6228 - 6239 (2010/11/02)
A series of N-(benzofuran-2-ylmethyl)-N′-benzylpiperazines bearing alkyl or fluoroalkyl aryl ethers were synthesized and evaluated at various central nervous system receptors. Examination of in vitro σ1 {[3H](+)-pentazocine} and σ2 ([3H]DTG) receptor binding profiles of piperazines 11-13 and 25-36 revealed several highly potent and σ1 selective ligands, notably, N-(benzofuran-2- ylmethyl)-N′-(4′-methoxybenzyl)piperazine (13, Ki = 2.7 nM, σ2/σ1 = 38) and N-(benzofuran-2-ylmethyl)- N′-(4′-(2″-fluoroethoxy)benzyl)piperazine (30, Ki = 2.6 nM, σ2/σ1 = 187). Structural features for optimal σ1 receptor affinity and selectivity over the σ2 receptor were identified. On the basis of its favorable log D value, 13 was selected as a candidate for the development of a σ1 receptor positron emission tomography radiotracer. [ 11C]13 showed high uptake in the brain and other σ receptor-rich organs of a Papio hamadryas baboon. The in vivo evaluation of [11C]13 indicates that this radiotracer is a suitable candidate for imaging the σ1 receptor in neurodegenerative processes.
Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
Asano, Keisuke,Matsubara, Seijiro
supporting information; experimental part, p. 1757 - 1759 (2009/09/06)
A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.
