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Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol.

Zhang T, Paluch K, Scalabrino G, Frankish N, Healy AM, Sheridan H - J Mol Struct (2015)

Bottom Line: The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1).The molecular and crystal structures of this novel compound have been fully analyzed.The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

View Article: PubMed Central - PubMed

Affiliation: Trino Therapeutics Ltd, The Tower, Trinity Technology and Enterprise Campus, Dublin 2, Ireland ; Novel Drug Discovery Group, School of Pharmacy and Pharmaceutical Sciences & Trinity Biomedical Sciences Institute, Trinity College, Dublin 2, Ireland.

ABSTRACT

The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1). The molecular and crystal structures of this novel compound have been fully analyzed. The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

No MeSH data available.


Expansions of aromatic regions of HMBC NMR spectrum of compound (4).
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f0060: Expansions of aromatic regions of HMBC NMR spectrum of compound (4).

Mentions: Correlation of H2 to a tertiary carbon, C4, at 125.7 ppm and a carbonyl carbon, C27, at most downfield at 165.6 ppm were evident from HMBC spectrum (Fig. 12). From HSQC spectrum (Fig. 11), it was clear that the H4 doublet at 7.39 ppm correlated with two carbon atoms at 125.7 and 126.9 ppm with unequal coupling intensities, suggesting the stronger and weaker contours to be C4 (at 125.7 ppm) and C5 (at 126.9 pm) respectively. HSQC analysis further indicated H5 with a resonance position of being centered at 7.23 ppm. A contour in HMBC spectrum indicative of correction of C5 to H7 (over three bonds) and H6 (over two bonds) demonstrated the overlapped signal in the region from 7.30 to 7.33 ppm was attributed to H6 and H7 (Fig. 8). Application of signal deconvolution resulted in the observations of an apparent doublet (at 7.311 ppm) and unwell-solved triplet (at 7.319 ppm), in which were accounted for H7 and H6 respectively (Fig. 10). Three-bond coupling existed between H7 and C9, which was found to resonate at 40.4 ppm in HMBC spectrum, while its corresponding proton, H9, presented at 3.19 and 3.371 ppm as two doublets (J = 15.42 Hz). These assignments were in agreement with the 1D selective TOCSY spectral data (Fig. 13).


Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol.

Zhang T, Paluch K, Scalabrino G, Frankish N, Healy AM, Sheridan H - J Mol Struct (2015)

Expansions of aromatic regions of HMBC NMR spectrum of compound (4).
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4308634&req=5

f0060: Expansions of aromatic regions of HMBC NMR spectrum of compound (4).
Mentions: Correlation of H2 to a tertiary carbon, C4, at 125.7 ppm and a carbonyl carbon, C27, at most downfield at 165.6 ppm were evident from HMBC spectrum (Fig. 12). From HSQC spectrum (Fig. 11), it was clear that the H4 doublet at 7.39 ppm correlated with two carbon atoms at 125.7 and 126.9 ppm with unequal coupling intensities, suggesting the stronger and weaker contours to be C4 (at 125.7 ppm) and C5 (at 126.9 pm) respectively. HSQC analysis further indicated H5 with a resonance position of being centered at 7.23 ppm. A contour in HMBC spectrum indicative of correction of C5 to H7 (over three bonds) and H6 (over two bonds) demonstrated the overlapped signal in the region from 7.30 to 7.33 ppm was attributed to H6 and H7 (Fig. 8). Application of signal deconvolution resulted in the observations of an apparent doublet (at 7.311 ppm) and unwell-solved triplet (at 7.319 ppm), in which were accounted for H7 and H6 respectively (Fig. 10). Three-bond coupling existed between H7 and C9, which was found to resonate at 40.4 ppm in HMBC spectrum, while its corresponding proton, H9, presented at 3.19 and 3.371 ppm as two doublets (J = 15.42 Hz). These assignments were in agreement with the 1D selective TOCSY spectral data (Fig. 13).

Bottom Line: The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1).The molecular and crystal structures of this novel compound have been fully analyzed.The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

View Article: PubMed Central - PubMed

Affiliation: Trino Therapeutics Ltd, The Tower, Trinity Technology and Enterprise Campus, Dublin 2, Ireland ; Novel Drug Discovery Group, School of Pharmacy and Pharmaceutical Sciences & Trinity Biomedical Sciences Institute, Trinity College, Dublin 2, Ireland.

ABSTRACT

The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1). The molecular and crystal structures of this novel compound have been fully analyzed. The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

No MeSH data available.