c-5-Hydroxy-r-2,c-4-bis(isopropoxycarbonyl)-t-5-methyl-t-3-phenylcyclohexanone

Hema, R.; Parthasarathi, V.; Ravikumar, K.; Pandiarajan, K.; Murugavel, K.

doi:10.1107/s1600536806001772

Cited by 4 publications

(6 citation statements)

References 10 publications

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“…The mean planes through C1, C3, C4 and C6 and ring A make a dihedral angle of 82.06 (12)°. This value is greater than that reported for a similar structure (73.76°) (Hema et al, 2006). The dihedral angle between ring A and the carboxy groups O2-C21-O3 and O6-C41-O4 are 61.14 (24)° and 74.71 (27)°, respectively.…”

Section: S1 Commentcontrasting

confidence: 63%

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c-5-Hydroxy-r-2,c-4-bis(methoxycarbonyl)-t-5-methyl-t-3-(3-nitrophenyl)cyclohexanone

Begum¹,

Hema²,

Pandiarajan³

et al. 2012

Acta Cryst E

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In the title compound, C17H19NO8 [systematic name = dimethyl 4-hydroxy-4-methyl-2-(3-nitrophenyl)-6-oxocyclohexane-1,3-dicarboxylate], the cyclohexanone ring exhibits a chair conformation. The methoxycarbonyl groups are oriented in opposite directions with respect to the cyclohexanone ring. In the crystal, O—H⋯O hydrogen bonds links the molecules into chains running parallel to the a axis. These chains are connected by weak C—H⋯O hydrogen bonds, forming sheets parallel to the ab plane.

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Section: S1 Commentcontrasting

confidence: 63%

“…For the pharmacological activity of cyclohexanone derivatives, see: Puetz et al(2003); Danyi et al (1989); For related structure, see: Hema et al (2006). For conformational analysis, see: Allinger (1977); Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

c-5-Hydroxy-r-2,c-4-bis(methoxycarbonyl)-t-5-methyl-t-3-(3-nitrophenyl)cyclohexanone

Begum¹,

Hema²,

Pandiarajan³

et al. 2012

Acta Cryst E

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“…The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anesthetic and antihistaminic drugs (Rajveer et al, 2010). As part of our studies in this area (Fatima et al, 2013;Hema et al, 2006), we have undertaken a single-crystal structure determination of the title compound.…”

Section: Methodsmentioning

confidence: 99%

“…For related structures, see: Fatima et al (2013); Hema et al (2006). For ring puckering parametes, see : Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

3-[(E)-2-(2-Methoxyphenyl)vinyl]-5,5-dimethylcyclohex-2-enone

et al. 2014

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.085; wR factor = 0.283; data-to-parameter ratio = 20.1.The title compound, C 17 H 20 O 2 , has an E conformation about the bridging C C bond. The cyclohexene ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. Its mean plane makes a dihedral angle of 7.20 (12) with the benzene ring. In the crystal, neighbouring molecules are connected via C-HÁ Á ÁO hydrogen bonds, forming chains running along the a-axis direction. Related literature

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“…NMR spectrum, , ppm: 20.6 (CH 3 i-Pr); 20.8 (CH 3 i-Pr); 27.6 (6-CH 3 ); 35.8 (C-7); 39.6 (C-4); 58.9 (C-5); 65.9 (CH i-Pr); 69.3 (C-6); 98.7 (C-9); 125.2-127.5 (Ar); 138.2 (C-8); 142.5 (ipso-C); 157.3 (C-3); 171.31 (C=O).t-4-p-Fluorophenyl-3,c-6-dihydroxy-6-methyl-1H-indazole-r-5-carboxylic Acid Isopropyl Ester(9). IR spectrum,  cm -1 : 3437, 3267 (OH and NH);1721 (CO group);1619 (C=N). 1 H NMR spectrum,, ppm(J, Hz):0.82 (3H, d, J = 6.1, CH 3 CH);1.09 (3H, d, J = 6.2, CH 3 CH); 1.21 (3H, s, 6-CH 3 ); 2.52 (2H, m, H-5a and H-7a); 2.76 (1H, d, J = 16.1, H-7e); 4.03 (1H, d, J = 10.6, H-4a); 4.42 (1H, s, 6-OH); 4.76 (1H, m, CHCH 3 ); 7.11 7.04 (4H, m, Ar); 8.92 (1H, br.…”

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confidence: 99%

A convenient synthesis and structural analysis of novel 4,5,6,7-tetrahydro-1H-indazoles

Murugavel¹,

Amirthaganesan²,

Mohan³

2010

Chem Heterocycl Comp

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isopropyl esters has been synthesized by adopting a conventional method from cyclic -keto esters. 1 H, 13 C NMR, and IR spectra for all the compounds were investigated. HMBC, HSQC, COSY, and NOESY spectra of the representative compounds were studied. The stereochemistry of a six-membered ring of the fused indazoles resembled that of keto esters. From the HMBC correlations the indazole structure was confirmed as 1H-indazole.The universal requirements on heterocyclic compounds for their potential activities against microorganisms and significance in the pharmaceutical field prompted us to synthesize indazoles from cyclic keto esters. Several pathways have been described for the synthesis of indazoles [1][2][3][4][5].Recently we reported the synthesis and structural studies of r-2,c-4-bis(alkoxycarbonyl)-t-3-arylc-5-hydroxy-t-5-methylcyclohexanone by the condensation of acetoacetic esters with different aromatic aldehydes in the presence of methylamine [6][7][8]. The conformation of the two isopropyl groups of compound 1 was also studied with the help of X-ray crystallography of t-2-aryl-c-4-hydroxy-4-methyl-6-oxocyclohexane-r-1,c-3-dicarboxylic acid diisopropyl ester [9]. The present paper describes the use of the above compounds [8] assynthons for the preparation of 4,5,6,7-tetrahydro-1H-indazole. The synthesis of 4,5-trans-2-alkyl-4-hetaryl-5-ethoxycarbonyl(acetyl)-6-hydroxy-6-methyl-4,5,6,7-tetrahydro-2H-indazole has been reported [10]. Nevertheless, the published NMR spectral data apliesmoreto1H-indazolethan to 2H-indazole. N(2)-Substituted tetrahydroindazoles have been reported in [11].Synthesis of 4,5,6,7-1H-indazoles involves two steps. The first step, condensation of isopropyl acetoacetate with aromatic aldehydes in the presence of methylamine in ethanol, yielded cyclic -keto esters 1-7. They were treated with hydrazine hydrate in ethanol under reflux to give compounds 8-14 (Scheme). The mechanism of this second step was different from the expected one. Dehydration was faster than cyclization, and the cyclic intermediates formed in the reaction course were unstable and easily underwent amido-imidol tautomerism, yielding stable 1H-indazoles.

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c-5-Hydroxy-r-2,c-4-bis(isopropoxycarbonyl)-t-5-methyl-t-3-phenylcyclohexanone

Abstract: Key indicatorsSingle-crystal X-ray study T = 273 K Mean (C-C) = 0.002 Å R factor = 0.037 wR factor = 0.104 Data-to-parameter ratio = 14.5For details of how these key indicators were automatically derived from the article, see

Cited by 4 publications

References 10 publications

c-5-Hydroxy-r-2,c-4-bis(methoxycarbonyl)-t-5-methyl-t-3-(3-nitrophenyl)cyclohexanone

c-5-Hydroxy-r-2,c-4-bis(methoxycarbonyl)-t-5-methyl-t-3-(3-nitrophenyl)cyclohexanone

3-[(E)-2-(2-Methoxyphenyl)vinyl]-5,5-dimethylcyclohex-2-enone

A convenient synthesis and structural analysis of novel 4,5,6,7-tetrahydro-1H-indazoles

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