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, C17H25N3O8, which released butylamine upon photoirradiation. Single crystals of the title...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023004103 |
| _version_ | 1797692275639189504 |
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| author | Takafumi Honda Michiko Ito Kazuo Yamaguchi Noriko Chikaraishi Kasuga Hiroyasu Sato |
| author_facet | Takafumi Honda Michiko Ito Kazuo Yamaguchi Noriko Chikaraishi Kasuga Hiroyasu Sato |
| author_sort | Takafumi Honda |
| collection | DOAJ |
| 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, C17H25N3O8, 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. |
| first_indexed | 2024-03-12T02:26:14Z |
| format | Article |
| id | doaj.art-a2fbc3a6ef354f428222f8eb7443665a |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-12T02:26:14Z |
| publishDate | 2023-06-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-a2fbc3a6ef354f428222f8eb7443665a2023-09-05T13:04:47ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-06-0179654955110.1107/S2056989023004103ex2069Synthesis and structure of photodegradable 1-(4,5-dimethoxy-2,3-dinitrophenyl)-2-methylpropyl N-butylcarbamateTakafumi Honda0Michiko Ito1Kazuo Yamaguchi2Noriko Chikaraishi Kasuga3Hiroyasu Sato4Department of Chemistry, Faculty of Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, JapanDepartment of Chemistry, Faculty of Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, JapanDepartment of Chemistry, Faculty of Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, JapanDepartment of Chemistry, Faculty of Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, JapanRigaku Corporation 3-9-12 Matsubara-cho, Akishima, Tokyo 196-8666, JapanThe 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, C17H25N3O8, 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.http://scripts.iucr.org/cgi-bin/paper?S2056989023004103photolabile carbamate2,3-dinitrobenzyl groupintermolecular hydrogen bondingcrystal structure |
| spellingShingle | Takafumi Honda Michiko Ito Kazuo Yamaguchi Noriko Chikaraishi Kasuga Hiroyasu Sato Synthesis and structure of photodegradable 1-(4,5-dimethoxy-2,3-dinitrophenyl)-2-methylpropyl N-butylcarbamate Acta Crystallographica Section E: Crystallographic Communications photolabile carbamate 2,3-dinitrobenzyl group intermolecular hydrogen bonding crystal structure |
| 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 | photolabile carbamate 2,3-dinitrobenzyl group intermolecular hydrogen bonding crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023004103 |
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