Literature DB >> 33953958

Syntheses and structures of two benzoyl amides: 2-chloro-4-eth-oxy-3,5-dimeth-oxy-N-(3-oxo-cyclo-hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl)-4-eth-oxy-3,5-di-meth-oxy-benzamide.

Alan J Anderson1, Ray J Butcher2, Edward Ollie1.   

Abstract

The first title benzoyl amide, C17H20ClNO5 (3a), crystallizes in the monoclinic space group P21/c with Z = 4 and the second, C19H24ClNO5 (3b), also crystallizes in P21/c with Z = 8 (Z' = 2), thus there are two independent mol-ecules in the asymmetric unit. In 3a, the phenyl ring makes a dihedral angle of 50.8 (3)° with the amide moiety with the C=O group on the same side of the mol-ecule as the C-Cl group. One meth-oxy group is almost in the plane of the benzene ring, while the eth-oxy and other meth-oxy substituent are arranged on opposite sides of the ring with the eth-oxy group occupying the same side of the ring as the C=O group in the amide moiety. For one of the two mol-ecules in 3b, both the amide and 5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl moieties are disordered over two sets of sites with occupancies of 0.551 (2)/0.449 (2) with the major difference between the two conformers being due to the conformation adopted by the cyclo-hex-2-en-1-one ring. The three mol-ecules in 3b (i.e., the undisordered mol-ecule and the two disorder components) differ in the arrangement of the subsituents on the phenyl ring and the conformation adopted by their 5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl moieties. In the crystal of 3a, N-H⋯O hydrogen bonds link the mol-ecules into a zigzag chain propagating in the [001] direction. For 3b a combination of C-H⋯O and N-H⋯O inter-molecular inter-actions link the mol-ecules into a zigzag ribbon propagating in the [001] direction. © Anderson et al. 2021.

Entities:  

Keywords:  bioactivity; crystal structure; enamino­nes

Year:  2021        PMID: 33953958      PMCID: PMC8061103          DOI: 10.1107/S2056989021001778

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  9 in total

1.  A short history of SHELX.

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2.  A base-catalyzed solution-phase parallel synthesis of substituted vinylic benzamides from 3-amino-2-cyclohexanones.

Authors:  Alan J Anderson; Jesse M Nicholson; Oladapo Bakare; Ray J Butcher; K R Scott
Journal:  J Comb Chem       Date:  2004 Nov-Dec

3.  Synthesis and anticonvulsant activity of enaminones. Part 7. Synthesis and anticonvulsant evaluation of ethyl 4-[(substituted phenyl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylates and their corresponding 5-methylcyclohex-2-enone derivatives.

Authors:  Natalie D Eddington; Donna S Cox; Manoj Khurana; Noha N Salama; James P Stables; Sylvia J Harrison; Abraham Negussie; Robert S Taylor; Uy Q Tran; Jacqueline A Moore; Judith C Barrow; K R Scott
Journal:  Eur J Med Chem       Date:  2003-01       Impact factor: 6.514

4.  Spectral signatures of intramolecular charge transfer process in beta-enaminones: a combined experimental and theoretical analysis.

Authors:  Ramprasad Misra; Abhijit Mandal; Madhuri Mukhopadhyay; D K Maity; S P Bhattacharyya
Journal:  J Phys Chem B       Date:  2009-08-06       Impact factor: 2.991

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Authors:  Ling-Hong Meng; Xiao-Ming Li; Cui-Ting Lv; Cai-Guo Huang; Bin-Gui Wang
Journal:  J Nat Prod       Date:  2014-08-22       Impact factor: 4.050

6.  Catalyst control over regio- and enantioselectivity in Baeyer-Villiger oxidations of functionalized ketones.

Authors:  David K Romney; Sean M Colvin; Scott J Miller
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419

7.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

8.  Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity.

Authors:  Joshua S Alford; Nadia C Abascal; Christopher R Shugrue; Sean M Colvin; David K Romney; Scott J Miller
Journal:  ACS Cent Sci       Date:  2016-09-13       Impact factor: 14.553

9.  Synthesis and in vitro protein tyrosine kinase inhibitory activity of furan-2-yl(phenyl)methanone derivatives.

Authors:  Fei Lang Zheng; Shu Rong Ban; Xiu E Feng; Cheng Xiao Zhao; Wenhan Lin; Qing Shan Li
Journal:  Molecules       Date:  2011-06-14       Impact factor: 4.411

  9 in total

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