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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.


(a) 1H NMR spectrum of compound (4); (b) 1D selective NOE spectrum of compound (4) following irradiation of signal at 8.05 ppm.
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f0070: (a) 1H NMR spectrum of compound (4); (b) 1D selective NOE spectrum of compound (4) following irradiation of signal at 8.05 ppm.

Mentions: HMBC spectrum illustrated correlations of C27 to a doublet (J = 8.52 Hz), H34 and H30, locating at most downfield 8.05 ppm via three-bond coupling (Fig. 12). Analysis of HSQC suggested correlations of H34 and C30 to an aromatic tertiary carbon at 131.3 ppm. The doublet at 8.05 ppm therefore represented two equivalent protons attached to C34 and C30. C32 was easily located at 128.5 ppm in HMBC spectrum over three-bond coupling to H34 and H30. Due to the electronegativity of bromine atom, the doublet (J = 8.68 Hz) at 7.67 ppm was believed to be account for H33 and H31, while their corresponding carbons, C33 and C31 had an overlapped chemical shift of 131.9 ppm. 1D selective NOE spectral data confirmed such assignments. Strong correlations between H34&H30 and H33&H31 were clearly observed (Fig. 14).


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)

(a) 1H NMR spectrum of compound (4); (b) 1D selective NOE spectrum of compound (4) following irradiation of signal at 8.05 ppm.
© Copyright Policy - CC BY
Related In: Results  -  Collection

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

f0070: (a) 1H NMR spectrum of compound (4); (b) 1D selective NOE spectrum of compound (4) following irradiation of signal at 8.05 ppm.
Mentions: HMBC spectrum illustrated correlations of C27 to a doublet (J = 8.52 Hz), H34 and H30, locating at most downfield 8.05 ppm via three-bond coupling (Fig. 12). Analysis of HSQC suggested correlations of H34 and C30 to an aromatic tertiary carbon at 131.3 ppm. The doublet at 8.05 ppm therefore represented two equivalent protons attached to C34 and C30. C32 was easily located at 128.5 ppm in HMBC spectrum over three-bond coupling to H34 and H30. Due to the electronegativity of bromine atom, the doublet (J = 8.68 Hz) at 7.67 ppm was believed to be account for H33 and H31, while their corresponding carbons, C33 and C31 had an overlapped chemical shift of 131.9 ppm. 1D selective NOE spectral data confirmed such assignments. Strong correlations between H34&H30 and H33&H31 were clearly observed (Fig. 14).

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.