About: Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates

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About: Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]helicenebisquinone I (R = dodecyl), which exhibits unique optical properties but previously was difficult to prep., and a variety of analogs. The synthesis starts from disodium 4,5-dihydroxynaphthalene-2,7-disulfonate, the com. available dye-intermediate known as chromotropic acid. It gives enantiopure I [R = (Me2CH)3Si] whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7-disulfonate, also an inexpensive, com. available chem., works equally well to produce the corresponding mols. that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate II [R1 = (Me2CH)3Si; R2 = (1S)-camphanoyl], the ester of the redn. A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]helicenebisquinone I (R = dodecyl), which exhibits unique optical properties but previously was difficult to prep., and a variety of analogs. The synthesis starts from disodium 4,5-dihydroxynaphthalene-2,7-disulfonate, the com. available dye-intermediate known as chromotropic acid. It gives enantiopure I [R = (Me2CH)3Si] whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7-disulfonate, also an inexpensive, com. available chem., works equally well to produce the corresponding mols. that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate II [R1 = (Me2CH)3Si; R2 = (1S)-camphanoyl], the ester of the redn. (en)
Title	Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates (en)
skos:prefLabel	Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates (en)
skos:notation	RIV/00216224:14310/00:00036039!RIV10-MSM-14310___
http://linked.open...avai/riv/aktivita	V
http://linked.open...avai/riv/aktivity	V
http://linked.open...iv/cisloPeriodika	65
http://linked.open...vai/riv/dodaniDat	2010
http://linked.open...aciTvurceVysledku	Paruch, Kamil
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	710810
http://linked.open...ai/riv/idVysledku	RIV/00216224:14310/00:00036039
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	helicene; Miura; preparation; optical properties (en)
http://linked.open.../riv/klicoveSlovo	optical properties helicene Miura preparation
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[E6EF213D9B9C]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...UplatneniVysledku	2000
http://linked.open...v/svazekPeriodika	2000
http://linked.open...iv/tvurceVysledku	Paruch, Kamil Katz, Thomas Incarvito, Christopher Rheingold, Arnold Vyklický, Libor
issn	0022-3263
number of pages	9 (xsd:int)
http://localhost/t...ganizacniJednotka	14310

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