Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate

The reaction of 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propan-1-ol and butyl­iso­cyanate using di­butyl­tin dilaurate as a catalyst afforded 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate, C(17)H(25)N(3)O(8), which released butyl­amine upon photoirradiation. Sing...

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Autores principales: Honda, Takafumi, Ito, Michiko, Yamaguchi, Kazuo, Kasuga, Noriko Chikaraishi, Sato, Hiroyasu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242739/
https://www.ncbi.nlm.nih.gov/pubmed/37288466
http://dx.doi.org/10.1107/S2056989023004103
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author Honda, Takafumi
Ito, Michiko
Yamaguchi, Kazuo
Kasuga, Noriko Chikaraishi
Sato, Hiroyasu
author_facet Honda, Takafumi
Ito, Michiko
Yamaguchi, Kazuo
Kasuga, Noriko Chikaraishi
Sato, Hiroyasu
author_sort Honda, Takafumi
collection PubMed
description The reaction of 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propan-1-ol and butyl­iso­cyanate using di­butyl­tin dilaurate as a catalyst afforded 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate, C(17)H(25)N(3)O(8), which released butyl­amine upon photoirradiation. Single crystals of the title compound were grown in a 1:1 mixed solution of hexane and ethyl acetate. Two nitro groups and one meth­oxy group are twisted out of the plane of the aromatic ring in the novel photo-protecting group. Inter­molecular hydrogen bonds are observed between N-butyl­carbamate moieties parallel to the a axis.
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spelling pubmed-102427392023-06-07 Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate Honda, Takafumi Ito, Michiko Yamaguchi, Kazuo Kasuga, Noriko Chikaraishi Sato, Hiroyasu Acta Crystallogr E Crystallogr Commun Research Communications The reaction of 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propan-1-ol and butyl­iso­cyanate using di­butyl­tin dilaurate as a catalyst afforded 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate, C(17)H(25)N(3)O(8), which released butyl­amine upon photoirradiation. Single crystals of the title compound were grown in a 1:1 mixed solution of hexane and ethyl acetate. Two nitro groups and one meth­oxy group are twisted out of the plane of the aromatic ring in the novel photo-protecting group. Inter­molecular hydrogen bonds are observed between N-butyl­carbamate moieties parallel to the a axis. International Union of Crystallography 2023-05-16 /pmc/articles/PMC10242739/ /pubmed/37288466 http://dx.doi.org/10.1107/S2056989023004103 Text en © Honda et al. 2023 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Honda, Takafumi
Ito, Michiko
Yamaguchi, Kazuo
Kasuga, Noriko Chikaraishi
Sato, Hiroyasu
Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title_full Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title_fullStr Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title_full_unstemmed Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title_short Synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl N-butyl­carbamate
title_sort synthesis and structure of photodegradable 1-(4,5-dimeth­oxy-2,3-di­nitro­phen­yl)-2-methyl­propyl n-butyl­carbamate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242739/
https://www.ncbi.nlm.nih.gov/pubmed/37288466
http://dx.doi.org/10.1107/S2056989023004103
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