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Wikipedia

2-Methyl-6-nitrobenzoic anhydride

May 09, 2024

2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent,[1][2] having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan).[3] The compound is often abbreviated MNBA.

2-Methyl-6-nitrobenzoic anhydride
Names
Preferred IUPAC name
2-Methyl-6-nitrobenzoic anhydride
Identifiers
  • 434935-69-0
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8648059
ECHA InfoCard 100.156.789
  • 10472648
UNII
  • EC8MK6FE8B Y
  • DTXSID60440549
  • InChI=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
    Key: YEKPNMQQSPHKBP-UHFFFAOYSA-N
  • InChI=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
    Key: YEKPNMQQSPHKBP-UHFFFAOYAB
  • CC1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC(=O)C2=C(C=CC=C2[N+](=O)[O-])C
Properties
C16H12N2O7
Molar mass 344.279 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Abstract edit

The reagent is used for synthetic reactions wherein medium- and large-sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure (Shiina macrolactonization).[4][5] 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 edit

References edit

  1. ^ . OChemOnline. Archived from the original on 2017-09-04.
  2. ^ Yahata, K.; Ye, N.; Iso, K.; Naini, S. R.; Yamashita, S.; Ai, Y.; Kishi, Y. (2017). "Unified Synthesis of Right Halves of Halichondrins A–C". J. Org. Chem. 82 (17): 8792–8807. doi:10.1021/acs.joc.7b01283. PMID 28741352.
  3. ^ 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.
  4. ^ 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): 1822–30. doi:10.1021/jo030367x. PMID 15058924.
  5. ^ 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): 196–233. doi:10.1246/bcsj.20130216.

External links edit

  • 2-Methyl-6-nitrobenzoic Anhydride (MNBA) doi:10.1002/047084289X.rn00956
  • Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium-Sized Ring doi:10.1002/chem.200500417
  • Total Synthesis of Iejimalide B. An Application of the Shiina Macrolactonization doi:10.1021/ol702129w

May 09, 2024
methyl, nitrobenzoic, anhydride, organic, acid, anhydride, also, known, shiina, reagent, having, structure, wherein, carboxylic, acids, undergo, intermolecular, dehydration, condensation, developed, 2002, prof, isamu, shiina, tokyo, university, science, japan,. 2 Methyl 6 nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent 1 2 having a structure wherein carboxylic acids undergo intermolecular dehydration condensation It was developed in 2002 by Prof Isamu Shiina Tokyo University of Science Japan 3 The compound is often abbreviated MNBA 2 Methyl 6 nitrobenzoic anhydride Names Preferred IUPAC name 2 Methyl 6 nitrobenzoic anhydride Identifiers CAS Number 434935 69 0 3D model JSmol Interactive image ChemSpider 8648059 ECHA InfoCard 100 156 789 PubChem CID 10472648 UNII EC8MK6FE8B Y CompTox Dashboard EPA DTXSID60440549 InChI InChI 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 2H3Key YEKPNMQQSPHKBP UHFFFAOYSA NInChI 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 2H3Key YEKPNMQQSPHKBP UHFFFAOYAB SMILES CC1 C C CC C1 N O O C O OC O C2 C C CC C2 N O O C Properties Chemical formula C 16H 12N 2O 7 Molar mass 344 279 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 Contents 1 Abstract 2 See also 3 References 4 External linksAbstract editThe reagent is used for synthetic reactions wherein medium and large sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure Shiina macrolactonization 4 5 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 editCondensation reaction Fischer Speier esterification Mitsunobu reaction Shiina esterification Steglich esterification Yamaguchi esterificationReferences edit Named Reagents OChemOnline Archived from the original on 2017 09 04 Yahata K Ye N Iso K Naini S R Yamashita S Ai Y Kishi Y 2017 Unified Synthesis of Right Halves of Halichondrins A C J Org Chem 82 17 8792 8807 doi 10 1021 acs joc 7b01283 PMID 28741352 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 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 30 doi 10 1021 jo030367x PMID 15058924 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 2 196 233 doi 10 1246 bcsj 20130216 External links edit2 Methyl 6 nitrobenzoic Anhydride MNBA doi 10 1002 047084289X rn00956 Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium Sized Ring doi 10 1002 chem 200500417 Total Synthesis of Iejimalide B An Application of the Shiina Macrolactonization doi 10 1021 ol702129w Retrieved from https en wikipedia org w index php title 2 Methyl 6 nitrobenzoic anhydride amp oldid 1105207082, wikipedia, wiki, book, books, library,

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