2-Methyl-6-nitrobenzoic anhydride

2-Methyl-6-nitrobenzoic anhydride
Names
IUPAC name
(2-Methyl-6-nitrobenzoyl) 2-methyl-6-nitrobenzoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.789
Properties
C16H12N2O7
Molar mass 344.28 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Methyl-6-nitrobenzoic anhydride is a condensing agent also known as the Shiina reagent,[1][2][3][4][5][6][7][8][9][10][11][12] having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan).[13] 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).[14][15] 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

References

  1. ↑ http://www.ochemonline.com/Named_Reagents
  2. ↑ Eiseman, J. L.; Bai, L.; Jung W.-H.; Moura-Letts, G.; Day, B. W.; Curran, D. P. (2008). "Improved Synthesis of 6-epi-Dictyostatin and Antitumor Efficacy in Mice Bearing MDA-MB231 Human Breast Cancer Xenografts". J. Med. Chem. 51 (21): 6650. doi:10.1021/jm800979v.
  3. ↑ Nicolaou, K. C.; Baker, T. M.; Nakamura, T. (2011). "Synthesis of the WXYZA′ Domain of Maitotoxin". J. Am. Chem. Soc. 133 (2): 220. doi:10.1021/ja109533y.
  4. ↑ Müller, S.; Mayer, T.; Sasse, F.; Maier, M. E. (2011). "Synthesis of a Pladienolide B Analogue with the Fully Functionalized Core Structure". Org. Lett. 13 (15): 3940. doi:10.1021/ol201464m.
  5. ↑ Yamamoto, A.; Ueda, A.; Brémond, P.; Tiseni, P. S.; Kishi, Y. (2012). "Total Synthesis of Halichondrin C". J. Am. Chem. Soc. 134 (2): 893. doi:10.1021/ja2108307.
  6. ↑ Ueda, A.; Yamamoto, A.; Kato, D.; Kishi, Y. (2014). "Total Synthesis of Halichondrin A, the Missing Member in the Halichondrin Class of Natural Products". J. Am. Chem. Soc. 136 (13): 5171. doi:10.1021/ja5013307.
  7. ↑ Beveridge, R. E.; Batey, R. A. (2014). "An Organotrifluoroborate-Based Convergent Total Synthesis of the Potent Cancer Cell Growth Inhibitory Depsipeptides Kitastatin and Respirantin". Org. Lett. 16 (9): 2322. doi:10.1021/ol500484f.
  8. ↑ Janetzko, J.; Batey, R. A. (2014). "Organoboron-Based Allylation Approach to the Total Synthesis of the Medium-Ring Dilactone (+)-Antimycin A1b". J. Org. Chem. 79 (16): 7415. doi:10.1021/jo501134d.
  9. ↑ Wünsch, S.; Breit, B. (2015). "Probing o-Diphenylphosphanyl Benzoate (o-DPPB)-Directed C－C Bond Formation: Total Synthesis of Dictyostatin". Chem. Eur. J. 21 (6): 2358. doi:10.1002/chem.201406252.
  10. ↑ Goodreid, J. D.; Da Silveira Dos Santos, E.; Batey, R. A. (2015). "A Lanthanide(III) Triflate Mediated Macrolactonization/Solid-Phase Synthesis Approach for Depsipeptide Synthesis". Org. Lett. 17 (9): 2182. doi:10.1021/acs.orglett.5b00781.
  11. ↑ Sato, E.; Tanabe, Y.; Nakajima, N.; Ohkubo, A.; Suenaga, K. (2016). "Total Synthesis of Biselyngbyolide B". Org. Lett. 18 (9): 2047. doi:10.1021/acs.orglett.6b00660.
  12. ↑ Ogawa, H.; Iwasaki, A.; Sumimoto, S.; Iwatsuki, M.; Ishiyama, A.; Hokari, R.; Otoguro, K.; Omura, S.; Suenaga, K. (2017). "Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium". Org. Lett. 19 (4): 890. doi:10.1021/acs.orglett.7b00047.
  13. ↑ Shiina, I.; Ibuka, R.; Kubota, M. (2002). "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". Chem. Lett. 31 (3): 286. doi:10.1246/cl.2002.286.
  14. ↑ Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. (2004). "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 Catalysts". J. Org. Chem. 69 (6): 1822. doi:10.1021/jo030367x.
  15. ↑ Shiina, I. (2014). "An Adventurous Synthetic Journey with MNBA from Its Reaction Chemistry to the Total Synthesis of Natural Products". Bull. Chem. Soc. Jpn. 87 (2): 196. doi:10.1246/bcsj.20130216.


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