Conformational analysis of 20-keto steroids. Single-crystal X-ray structure analysis of 16α,17-epoxy-4-pregnene-3,20-dione

Schenk, H.; Zeelen, F. J.

doi:10.1016/s0039-128x(84)90081-3

Cited by 11 publications

(7 citation statements)

References 7 publications

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“…The bond distances and bond angles are in good agreement with the corresponding values obtained in case of 16α-17-epoxy-4-pregnene-3, 20-dione [13]; 21-hydroxy-11β,18-oxido-4-pregnene-3,20-dione [14]; pregnenolone hemisuccinate [15]; and 17α-acetoxy-6,7-epoxypregn-4-ene-3,20-dione [16]. Mean bond lengths for C(sp 3 )-C(sp 3 ) and C(sp 2 ) = O for compound 7 are 1.529 (7), 1.197 (7) Å, respectively.…”

Section: Structure Detailssupporting

confidence: 88%

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Crystal Structure and Synthesis of 3β-(p-Iodobenzoyloxy)-16α,17α-Epoxypregn-4-En-6,20-Dione

Chávez‐Riveros¹,

Cabeza²,

Bratoeff³

et al. 2014

CSTA

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How to cite this paper: Chávez-Riveros, A., Cabeza, M., Bratoeff, E. and Soriano-García, M. (2014) Crystal Structure and Synthesis of 3β-(p-Iodobenzoyloxy)-16α,17α-Epoxypregn-4-En-6,20-Dione. Crystal Structure Theory and Applications, 3, 39-47. http://dx.Abstract 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-en-6,20-dione (7), C 28 H 31 O 5 I, was synthesized from the commercially available 16-dehydropregnenolone acetate. X-ray diffraction analysis of (1) demonstrated that it consisted of four rings, three six-membered rings (A, B and C) and one fivemembered ring (D). A, B, C and D rings occur in an envelope, deformed chair, deformed chair, and the half chair conformations, respectively. The absolute configurations of 7 for the chiral centers are 3S, 8S, 9S, 10R, 13S and 14S. The crystal of 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-en-6,20-dione is in monoclinic crystal system with space group P21, lattice constants: a = 10.8567 (11), b = 7.5479 (7), c = 16.0391 (16) Å, β = 109.473 (1)˚, V = 1239.1 (2) Å 3 , Dx = 1.518 g/cm 3 and Z = 2. The molecules in the crystal are stabilized by C-H···O interactions and van der Waals forces.

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Section: Structure Detailssupporting

confidence: 88%

“…The crude product was recrystallized from methanol. 13 C-NMR (CDCl 3 ) δ: 18.7 (C-18), 20.1 (C-18), 67.6 (C-16), 69.9 (C-3), 79.5 (C-17), 129.1 (C-4), 147.8 (C-5), 201.6 (C-6). MS m/z 574 (M + ).…”

Section: Synthesis Of the Compound 3β-(p-iodobenzoyloxy)-16α17α-epoxmentioning

confidence: 99%

Crystal Structure and Synthesis of 3β-(p-Iodobenzoyloxy)-16α,17α-Epoxypregn-4-En-6,20-Dione

Chávez‐Riveros¹,

Cabeza²,

Bratoeff³

et al. 2014

CSTA

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“…Ring A is in a 1-sofa conformation, rings B and C are in nearly perfect chair conformations and ring D is in a 14-envelope conformation. The presence of the three-membered ring constrains ring D to have a 14-envelope conformation (Goubitz et al, 1984). The two molecules in the asymmetric unit have similar conformations.…”

Section: Commentmentioning

confidence: 99%

16α,17-Epoxy-11α-(p-tolylsulfonyloxy)pregn-4-ene-3,20-dione

Nie

Wang

et al. 2005

Acta Cryst E

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“…Ring A of (I) is in the 1-sofa conformation, whereas rings B and C are in chair conformations and ring D is in a 14envelope conformation. The conformations are similar to those in 17-hydroxyprogesterone (Declercq et al, 1972; refcode HPRGDO in the Cambridge Structural Database,-Version 5.25; Allen, 2002), and 16,17-epoxy-4-pregnene-3,20dione (refcode DILYEC; Goubitz et al, 1984).…”

Section: Commentmentioning

confidence: 55%

16β-Bromo-17α-hydroxypregn-4-ene-3,20-dione methanol solvate

Wang¹,

Wang²,

Nie³

et al. 2005

Acta Cryst E

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Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.012 Å R factor = 0.066 wR factor = 0.192 Data-to-parameter ratio = 15.0For details of how these key indicators were automatically derived from the article, see Figure 1 ORTEPII view (Johnson, 1976) of the title compound, shown with 30% probability displacement ellipsoids.organic papers o564 Shi Wang et al. C 21 H 29 BrO 3 ÁCH 4 O Acta Cryst. (2005). E61, o563-o564Figure 2The molecular packing of the title compound, viewed along the c axis.Dashed lines indicate the intermolecular hydrogen-bonding interactions

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Conformational analysis of 20-keto steroids. Single-crystal X-ray structure analysis of 16α,17-epoxy-4-pregnene-3,20-dione

Cited by 11 publications

References 7 publications

Crystal Structure and Synthesis of 3<i>β</i>-(<i>p</i>-Iodobenzoyloxy)-16<i>α</i>,17<i>α</i>-Epoxypregn-4-En-6,20-Dione

Crystal Structure and Synthesis of 3<i>β</i>-(<i>p</i>-Iodobenzoyloxy)-16<i>α</i>,17<i>α</i>-Epoxypregn-4-En-6,20-Dione

16α,17-Epoxy-11α-(p-tolylsulfonyloxy)pregn-4-ene-3,20-dione

16β-Bromo-17α-hydroxypregn-4-ene-3,20-dione methanol solvate

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Conformational analysis of 20-keto steroids. Single-crystal X-ray structure analysis of 16α,17-epoxy-4-pregnene-3,20-dione

Cited by 11 publications

References 7 publications

Crystal Structure and Synthesis of 3&lt;i&gt;β&lt;/i&gt;-(&lt;i&gt;p&lt;/i&gt;-Iodobenzoyloxy)-16&lt;i&gt;α&lt;/i&gt;,17&lt;i&gt;α&lt;/i&gt;-Epoxypregn-4-En-6,20-Dione

Crystal Structure and Synthesis of 3&lt;i&gt;β&lt;/i&gt;-(&lt;i&gt;p&lt;/i&gt;-Iodobenzoyloxy)-16&lt;i&gt;α&lt;/i&gt;,17&lt;i&gt;α&lt;/i&gt;-Epoxypregn-4-En-6,20-Dione

16α,17-Epoxy-11α-(p-tolylsulfonyloxy)pregn-4-ene-3,20-dione

16β-Bromo-17α-hydroxypregn-4-ene-3,20-dione methanol solvate

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Crystal Structure and Synthesis of 3<i>β</i>-(<i>p</i>-Iodobenzoyloxy)-16<i>α</i>,17<i>α</i>-Epoxypregn-4-En-6,20-Dione

Crystal Structure and Synthesis of 3<i>β</i>-(<i>p</i>-Iodobenzoyloxy)-16<i>α</i>,17<i>α</i>-Epoxypregn-4-En-6,20-Dione