- Synthesis of polyfluorinated ethers
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Procedures for preparing polyfluorinated ethers H(CF2CF 2)nCH2OR by alkylation of the corresponding telomeric alcohols H(CF2CF2)nCH2OH (n = 1-3) with alkyl halides and alkyl tosylates were examined.
- Bazhin,Gorbunova,Zapevalov,Saloutin
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Read Online
- A preparing method of diethylamino hydroxybenzoyl hexylbenzoate
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The present invention relates to a method for the preparation of diethylamino hydroxybenzoyl hexyl benzoate. Specifically, the present invention relates to a method for preparing diethylamino hydroxybenzoyl hexyl benzoate which is easy to manufacture and commercially available in mass production, and diethylamino hydroxybenzoyl hexyl benzoate crystalline particles prepared thereby. According to the present invention, diethylamino hydroxybenzoyl hexyl benzoate crystalline particles having excellent UV blocking effect can be obtained in a stable and high yield.COPYRIGHT KIPO 2020
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Paragraph 0081-0083
(2020/03/28)
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- Combinatorial discovery of thermoresponsive cycloammonium ionic liquids
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This work demonstrated, for the first time, the combinatorial discovery and rational identification of small-molecule cycloammonium-based thermoresponsive ionic liquids that exhibit LCST phase transition and carry attractiveTcvalues in water.
- Chu, Yen-Ho,Hwang, Chun-Chieh,Chen, Chien-Yuan,Tseng, Min-Jen
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p. 11855 - 11858
(2020/10/13)
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- Method for preparing N,N-Dimethylaniline compound through alkylation of alkyl tosylate
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The invention provides a method for preparing a N,N-Dimethylaniline compound through alkylation of alkyl tosylate, and belongs to the technical field of organic synthesis. According to the method, paratoluensulfonyl chloride and fatty alcohol serve as raw materials, pyridine serves as an acid-binding agent, and the alkyl tosylate is generated; the alkyl tosylate as an alkylation reagent and an aniline compound are alkylated under the alkaline condition to obtain the N,N-Dimethylaniline compound. The method is implemented at normal pressure, the operation is simple, no waste acid is generated,the yield and the purity are high, and the method is suitable for industrial and scaled production.
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Paragraph 0064-0065; 0068; 0071; 0074; 0077
(2019/07/11)
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- Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water
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A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.
- Feng, Simin,Li, Jing,Wei, Junfa
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supporting information
p. 4743 - 4746
(2017/07/12)
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- Trifluoromethylation of Alkyl Radicals in Aqueous Solution
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The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of Et3SiH and K2S2O8 initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF3)3 (BPy = 2,2′-bipyridine) in aqueous acetone at room temperature to afford the corresponding trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl halides and exhibits wide functional group compatibility. A mechanism involving trifluoromethyl group transfer from Cu(II)-CF3 intermediates to alkyl radicals is proposed.
- Shen, Haigen,Liu, Zhonglin,Zhang, Pei,Tan, Xinqiang,Zhang, Zhenzhen,Li, Chaozhong
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p. 9843 - 9846
(2017/08/02)
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- Hexyl triazabutadiene as a potent alkylating agent
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Alkyl diazonium ions are among the most reactive alkylating agents in the synthetic chemists’ arsenal. That said, there are precious few methods by which one can selectively and safely utilize this chemistry. Herein, we show the use of a bench stable hexyl triazabutadiene as a source of reactive diazonium ions that undergo substitution chemistry with weak nucleophiles, such as carboxylates and even sulfonates. In the absence of a nucleophile, elimination was observed to occur. To overcome issues stemming from side-product inhibition of the reaction, we show that the triazabutadiene can be pre-activated with tosyl isocyanate.
- Knyazeva, Diana C.,Kimani, Flora W.,Blanche, Jean-Laurent,Jewett, John C.
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p. 2700 - 2702
(2017/06/23)
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- A [...] analogs, its preparation process and its application
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The invention discloses a largazole analogue which contains alkyl disulfide side chains and is represented by formula I, and a preparation method and applications thereof. The largazole analogue possesses relatively high antineoplastic activity and selectivity, can be used for development of antitumor drugs. Raw materials of the largazole analogue are cheap and easily available; and the preparation method is simple, and is a method suitable for industrialization. R in formula represents an alkyl group containing 1 to 8 carbon atoms.
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Paragraph 0143-0146
(2016/10/08)
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- Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions
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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
- Gao, Jian,Pan, Xiaojun,Liu, Juan,Lai, Junyi,Chang, Liming,Yuan, Gaoqing
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p. 27439 - 27442
(2015/03/31)
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- Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity
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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.
- Timko, Luká?,Fischer-Fodor, Eva,Garajová, Mária,Mrva, Martin,Chereches, Gabriela,Ondriska, Franti?ek,Bukovsky, Marián,Luká?, Milo?,Karlovská, Janka,Kubincová, Janka,Devínsky, Ferdinand
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p. 263 - 273
(2015/05/26)
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- Design, synthesis, and biological evaluation of largazole derivatives: Alteration of the zinc-binding domain
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A new series of largazole analogues in which the side chain was replaced with disulfide groups were synthesized, and their biological activities were evaluated. Compound 8 bearing an octyl moiety showed much better selectivity for HDAC1 over HDAC7 than largazole (320-fold). Structure-activity relationships suggested that the length in the disulfide chain of largazole is important for the selectivity toward HDAC1 over HDAC7.
- Su, Jinyue,Qiu, Yatao,Ma, Kun,Yao, Yiwu,Wang, Zhen,Li, Xianling,Zhang, Dayong,Tu, Zhengchao,Jiang, Sheng
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p. 7763 - 7769
(2014/12/10)
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- Copper-catalyzed/promoted cross-coupling of gem -diborylalkanes with nonactivated primary Alkyl halides: An alternative route to alkylboronic esters
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The first copper-catalyzed/promoted sp3-C Suzuki-Miyaura coupling reaction of gem-diborylalkanes with nonactivated electrophilic reagents is reported. Not only 1, 1-diborylalkanes but also some other gem-diborylalkanes can be coupled with nonactivated primary alkyl halides, offering a new method for sp3C-sp3C bond formation and, simultaneously, providing a new strategy for the synthesis of alkylboronic esters.
- Zhang, Zhen-Qi,Yang, Chu-Ting,Liang, Lu-Jun,Xiao, Bin,Lu, Xi,Liu, Jing-Hui,Sun, Yan-Yan,Marder, Todd B.,Fu, Yao
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supporting information
p. 6342 - 6345
(2015/01/16)
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- Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides
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A copper-catalyzed reductive cross-coupling reaction of nonactivated alkyl tosylates and mesylates with alkyl and aryl bromides was developed. It provides a practical method for efficient and cost-effective construction of aryl-alkyl and alkyl-alkyl C=C bonds with stereocontrol from readily available substrates. When used in an intramolecular fashion, the reaction enables convenient access to various substituted carbo- or heterocycles, such as 2,3-dihydrobenzofuran and benzochromene derivatives.
- Liu, Jing-Hui,Yang, Chu-Ting,Lu, Xiao-Yu,Zhang, Zhen-Qi,Xu, Ling,Cui, Mian,Lu, Xi,Xiao, Bin,Fu, Yao,Liu, Lei
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supporting information
p. 15334 - 15338
(2016/02/18)
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- Copper-catalyzed reduction of alkyl triflates and iodides: An efficient method for the deoxygenation of primary and secondary alcohols
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We describe an effective method for catalytic reduction of 1°alkyl sulfonates, and 1°and 2°iodides in the presence of a wide range of functional groups. This Cu-catalyzed reaction provides a means for the effective deoxygenation of alcohols, as demonstrated by the highly selective reduction of 1°alcohols using a triflation/reduction sequence. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Primarily reduced: The copper-catalyzed reduction of 1°alkyl sulfonates, and 1°and 2°iodides, which is effective in the presence of a wide range of functional groups, provides a means for the effective deoxygenation of alcohols. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Copyright
- Dang, Hester,Cox, Nick,Lalic, Gojko
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supporting information
p. 752 - 756
(2014/01/23)
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- NHC-copper hydrides as chemoselective reducing agents: Catalytic reduction of alkynes, alkyl triflates, and alkyl halides
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The NHC-copper-catalyzed Z-selective semi-reduction of terminal and internal alkynes, as well as the NHC-copper-catalyzed reduction of primary alkyl triflates and primary and secondary alkyl iodides and bromides are described. The high chemoselectivity demonstrated in these examples illustrates the mild nature of copper hydride complexes as reducing agents, which have applications in synthetic chemistry beyond their traditional role in the reduction of activated alkenes and carbonyl compounds.
- Cox, Nick,Dang, Hester,Whittaker, Aaron M.,Lalic, Gojko
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p. 4219 - 4231
(2014/06/09)
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- Alkylboronic esters from copper-catalyzed borylation of primary and secondary alkyl halides and pseudohalides
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Easy access: An unprecedented copper-catalyzed cross-coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts=4-toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means. Copyright
- Yang, Chu-Ting,Zhang, Zhen-Qi,Tajuddin, Hazmi,Wu, Chen-Cheng,Liang, Jun,Liu, Jing-Hui,Fu, Yao,Czyzewska, Maria,Steel, Patrick G.,Marder, Todd B.,Liu, Lei
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supporting information; experimental part
p. 528 - 532
(2012/02/04)
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- Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides
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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.
- Yang, Chu-Ting,Zhang, Zhen-Qi,Liu, Yu-Chen,Liu, Lei
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supporting information; experimental part
p. 3904 - 3907
(2011/05/15)
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- Rearrangement of lithiated S-alkyl O,O-dialkyl thiophosphates: Scope and stereochemistry of the thiophosphate-mercaptophosphonate rearrangement
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S-Alkyl O,O-dialkyl thiophosphates are prepared by alkylation of the triethylammonium salt of O,O-diisopropyl thiophosphoric acid. S-Benzyl thiophosphate was metallated at temperatures of ≥-45 °C by trityllithium and LiTMP (lithium 2,2,6,6-tetramethylpiperidide) and S-alkyl thiophosphates only by LiTMP to give dipole-stabilised carbanions which rearrange to α-mercaptophosphonates in yields of up to 45%. Metallation occurs with a high primary kinetic isotope effect (kH/kD up to ≈50). When the lithium (R)-N-isopropyl-1-phenylethylamide was used to induce the isomerisation of S-pentyl thiophosphate an α-mercaptophosphonate with an ee of 22% was isolated. (R)-S-[1-D1]hexyl O,O-diisopropyl thiophosphate was rearranged to a dextrorotary α-mercapto-[1-D 1]hexylphosphonate, whose (R)-configuration was determined by chemical correlation. The thiophosphate-mercaptophosphonate rearrangement proceeds with retention of configuration. The Royal Society of Chemistry 2011.
- Philippitsch, Violeta,Hammerschmidt, Friedrich
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experimental part
p. 5220 - 5227
(2011/08/10)
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- Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
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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.
- Asano, Keisuke,Matsubara, Seijiro
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supporting information; experimental part
p. 1757 - 1759
(2009/09/06)
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- Synthesis and properties of 2-phenylbenzoxazole-based luminophores for in situ photopolymerized liquid-crystal films
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We report the synthesis of a series of blue-emitting 2-phenylbenzoxazoles (PBOs) substituted at either the 5- or 6-position of the benzoxazole ring and the para-position of the phenyl substituent. The thermal and optical properties of the materials can be rationalized in terms of the position of the substituent at the benzoxazole moiety and the electron-withdrawing or electron-donating character of the substituents. From the results, we conclude that the combination of an electron-donating substituent at the benzoxazole fragment and an electron-withdrawing one at the phenyl fragment has a more marked effect on the electronic properties of the aromatic PBO core than other possibilities. This particular combination gives luminophores that are suitable for optical applications on the basis of their high emission efficiency and photostability. In view of that, oriented films were prepared by in situ polymerization of a mixture of a liquid crystalline direactive matrix containing 5% (w/w) of the luminophore. The films exhibit linearly polarized emission.
- Gimenez, Raquel,Oriol, Luis,Pinol, Milagros,Serrano, Jose Luis,Vinuales, Ana I.,Fisher, Thomas,Stumpe, Joachim
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p. 304 - 319
(2007/10/03)
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- An efficient one pot synthesis of carbamate esters through alcoholic tosylates
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An efficient O-alkylation of alcoholic tosylates with amines in a K2CO3/CO2 system in the presence of tetrabutyl ammonium iodide (TBAI) provides exclusive formation of carbamates.
- Chaturvedi, Devdutt,Kumar, Atul,Ray
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p. 2651 - 2655
(2007/10/03)
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- Process for preparation of oxyglutaric acid ester derivatives
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A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.
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- Mesomorphic compound, liquid crystal composition and liquid crystal device using same
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 and R2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of having a substituent; X denotes any one of a single bond, --O--, STR2 Y denotes STR3 or --CH2 O--; and Z denotes any one of --O--, STR4 .
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- Evaluation of the quantitative contribution of an aryl group on C(2) of 8-azaadenines to binding with adenosine deaminase: A new synthesis of 8-azaadenosine. XI
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The introduction of a phenyl group on C(2) of 8-azaadenosine increases binding to the adenosine deaminase enzyme (ADA). This stability increment has been quantitatively evaluated in both 8-azaadenosines and 9-(2',3'-dihydroxypropyl)-8-azaadenines; it resulted nearly equivalent in the two series. 8-Azaadenosine has been synthesized through a new route employing fully protected β-D-ribofuranosyl-1-azide. Instead, the stability difference in 9-(n-alkyl)-8-azaadenines, owing to the inactivity of the C(2) unsubstituted compounds, could not be evaluated. Consideration of the enantioselectivity of the ADA enzyme toward chiral 9-(2',3'-dihydroxypropyl)-8-azaadenines and 9-(2',3'-dihydroxypropyl)-8-azahypoxanthines allowed the exclusion of an appreciable structural modification in the enzyme-inhibitor complex when hydrogen on C(2) is substituted by an aryl group.
- Biagi,Giorgi,Livi,Scartoni,Lucacchini
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p. 1457 - 1476
(2007/10/02)
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- REACTION OF PHOSPHORUS OXYACID ESTERS WITH p-TOLUENESULFONIC ACID
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The reaction of primary alkyl esters of phosphorus oxyacids with p-toluenesulfonic acid (TsOH) in refluxing solvents gave the corresponding p-toluenesulfonates (TsOR).We found that the secondary alkyl esters reacted with TsOH at lower temperature (r.t.-40 deg C) to afford TsORs in good yields.It is suggested that sulfonic acids may be useful for the selective dealkylation of mixed esters.Keywords-p-toluenesulfonic acid; p-toluenesulfonate; trialkyl phosphate; trialkyl phosphite; dialkyl phenylphosphonate; transesterification; dealkylation; solvolysis.
- Nitta, Yoshihiro,Arakawa, Yasushi,Ueyama, Naoto
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p. 2710 - 2718
(2007/10/02)
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- Oxidatively Assisted Nucleophic Substitution of Iodine in Alkyl Iodides by Nucleofugic Anions
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The reaction of alkyl iodides with chlorine or nitronium tetrafluoroborate in the presence of salts of perchloric or substitued sulfonic acids gave alkyl perchlorates or sulfonates as principal products.Some mechanistic aspects of this new reaction are discussed.
- Zefirow, Nikolai S.,Zhdankin, Victor V.,Makhon'kova, Galina V.,Dan'kov, Yuri V.,Koz'min, Anatoly S.
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p. 1872 - 1876
(2007/10/02)
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- Reaction of Carboxylic Acid Esters with p-Toluenesulfonic Acid
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The reaction of carboxylic acid esters with an excess of p-toluenesulfonic acid gave the corresponding p-toluenesulfonates.The mechanism of the transesterification is discussed.
- Nitta, Yoshihiro,Arakawa, Yasushi
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p. 1380 - 1386
(2007/10/02)
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