2-Methyl-6-nitrobenzoic anhydride

2-Methyl-6-nitrobenzoic anhydride.svg 2-Methyl-6-nitrobenzoic anhydride 434935-69-0 correct FDA EC8MK6FE8B 10472648 CC1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC(=O)C2=C(C=CC=C2[N+](=O)[O-])C 8648059 1/C16H12N2O7/c1-9-5-3-7-11(17(21)22)13(9)15(19)25-16(20)14-10(2)6-4-8-12(14)18(23)24/h3-8H,1-2H3 YEKPNMQQSPHKBP-UHFFFAOYAB 1S/C16H12N2O7/c1-9-5-3-7-11(17(21)22)13(9)15(19)25-16(20)14-10(2)6-4-8-12(14)18(23)24/h3-8H,1-2H3 YEKPNMQQSPHKBP-UHFFFAOYSA-N 16 12 2 7 2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent,http://www.ochemonline.com/Named_Reagents Named Reagents https://web.archive.org/web/20170904105636/http://www.ochemonline.com/Named_Reagents OChemOnline 2017-09-04 deadYahata, K. Ye, N. Iso, K. Naini, S. R. Yamashita, S. Ai, Y. Kishi, Y. J. Org. Chem. 2017 8792–8807 10.1021/acs.joc.7b01283 28741352 82 17 Unified Synthesis of Right Halves of Halichondrins A–C having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan).Shiina, I. Ibuka, R. Kubota, M. Chem. Lett. 2002 286 10.1246/cl.2002.286 31 3 A New Condensation Reaction for the Synthesis of Carboxylic Esters from Nearly Equimolar Amounts of Carboxylic Acids and Alcohols Using 2-Methyl-6-nitrobenzoic Anhydride The compound is often abbreviated MNBA. Abstract The reagent is used for synthetic reactions wherein medium- and large-sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure (Shiina macrolactonization).Shiina, I. Kubota, M. Oshiumi, H. Hashizume, M. J. Org. Chem. 2004 1822–30 10.1021/jo030367x 15058924 69 6 An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic CatalystsShiina, I. Bull. Chem. Soc. Jpn. 2014 196–233 10.1246/bcsj.20130216 87 2 An Adventurous Synthetic Journey with MNBA from Its Reaction Chemistry to the Total Synthesis of Natural Products free The reaction proceeds at room temperature under basic or neutral conditions. This reagent can be used not only for macrolactonization but also for esterification, amidation, and peptide coupling. See also Condensation reaction Fischer-Speier esterification Mitsunobu reaction Shiina esterification Steglich esterification Yamaguchi esterification References External links 2-Methyl-6-nitrobenzoic Anhydride (MNBA) 10.1002/047084289X.rn00956 Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium-Sized Ring 10.1002/chem.200500417 Total Synthesis of Iejimalide B. An Application of the Shiina Macrolactonization 10.1021/ol702129w Category:Carboxylic anhydrides Category:Nitrobenzene derivatives