scholarly journals A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

2014 ◽  
Vol 10 ◽  
pp. 1390-1396 ◽  
Author(s):  
Martin Popr ◽  
Simona Hybelbauerová ◽  
Jindřich Jindřich
Keyword(s):  
Chromatographic Separation ◽  
Functional Group ◽  
Single Step ◽  
Starting Material ◽  
Scale Production ◽  
Synthetic Route ◽  
Complete Series ◽  
Work Up ◽  
Derivatives Of

An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N’-trimethylethane-1,2-diamine or N,N,N’-trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.

Toxicity of Para-Chloro Substituted Benzene Derivatives in the Microtox™ Test

1985 ◽  
Vol 20 (2) ◽  
pp. 36-43 ◽  
Author(s):  
Klaus L.E. Kaiser ◽  
Juan M. Ribo ◽  
Brian M. Zaruk
Keyword(s):  
General Formula ◽  
Functional Group ◽  
Structural Parameters ◽  
Systematic Investigation ◽  
Photobacterium Phosphoreum ◽  
Benzene Derivatives ◽  
Quantitative Structure ◽  
Chlorinated Benzenes ◽  
Chloro Derivatives ◽  
Derivatives Of

Abstract This paper gives the results of part of a systematic investigation into contaminant toxicity to Photobacterium phosphoreum in the Microtox™ test. Reported are the toxicity values for 39 para-chloro substituted benzene derivatives of the general formula l-Cl-C6h4-4-X=CH2CH(NH2)COOH, F, SO2NH2, OCH2COOH, CH2COOH, CONHNH2, NHCOCH3, CONH2, CH=CHCOOH, SeOOH, CH2NH2, CH2CH2NH2, NO2, H, CF3, CHO, CH2OH, OH, CH3, CCl3, COCH3, COOH, NH2, SO2C6H5, Cl, CH2COCH3, COCl, CN, OCH3, NCO, NHCH3, I, COC6H5, CH2Cl, SH, CH2SH, NCS, CH2CN and SO2C6H4Cl. Except for the last compound, whose solubility is below the required concentration, the toxicities increase in the presented order with a total range of more than three orders of magnitude. The data are discussed in terms of quantitative structure-toxicity correlations with compound-specific structural parameters. In combination with a previously developed submodel on chlorinated benzenes, phenols, nitrobenzenes and anilines, the observed relationships allow the prediction of the toxicity of some 780 possible chloro derivatives of the general formula C6H5-nClnX, where n=<5 and X is a functional group as listed above.

SYNTHESIS OF 1,1,1-TRICHLORO-2,2-BIS-(p-CYANOPHENYL)-ETHANE

1952 ◽  
Vol 30 (3) ◽  
pp. 203-207 ◽  
Author(s):  
Yvon Perron ◽  
Roger Barré
Keyword(s):  
Condensation Product ◽  
Starting Material ◽  
Derivatives Of

The synthesis of 1,1,1-trichloro-2,2-bis-(p-cyanophenyl)-ethane was carried out with the condensation product of chloral and toluene as starting material. This product was converted, through the corresponding tetraacetate, to 1,1,1-trichloro-2,2-bis-(p-aldehydophenyl)-ethane which in turn reacted with hydroxylamine to give the dioxime. The subsequent dehydration of the latter gave rise to the desired dinitrile. The corresponding dichloro derivatives of the oxime and nitrile were also prepared.

scholarly journals Antimonial analogues of the acridine series. Dilhydrostibacridines

1933 ◽  
Vol 143 (848) ◽  
pp. 38-47 ◽  
Keyword(s):  
Nitro Derivative ◽  
Starting Material ◽  
Arsenic Compounds ◽  
Ring Systems ◽  
Nitrogen Ring ◽  
Derivatives Of

In pursuing our investigation out the antimony analogues of certain nitrogen ring-systems, we Lave now succeeded in obtaining derivatives of dilhydrostibacridines, of when some of the corresponding arsenic compounds have been studied recently by Gump and Stolzenburg. The starting material for the work was o -aminodiphenylmethane obtained from the corresponding nitro derivative when, in turn, was prepared from o -nitrobenzyl chloride and benzene by Taneseseu's modification of the Friedel-Crafts reaction.

A Synthetic Route to Epoxyalkyl β-Laminaribiosides, Especially Suitable for Radiolabeling

1994 ◽  
Vol 47 (9) ◽  
pp. 1805 ◽  
Author(s):  
WM Best ◽  
RV Stick ◽  
DMG Tilbrook
Keyword(s):  
Synthetic Route ◽  
Benzyl Ethers ◽  
Derivatives Of

The major products in the controlled benzylation (NaH/PhCH2Cl) of allyl and but-3-enyl β-D-glucopyranosides were the 2,4,6-tri-O-benzyl ethers. Subsequent glycosidations of these tribenzyl ethers gave derivatives of allyl and but-3-enyl β- laminaribioside, the latter being subsequently transformed into 3,4-epoxybutyl β- laminaribioside.

Sign in / Sign up

Export Citation Format

Share Document