1,1′,1′′-[(5RS,6RS)-6-Hydroxy-6-methyl-3,4,5,6-tetrahydro-2H-pyran-3,3,5-triyl]triethanone

Burton, Sylvester; Fronczek, Frank R.; Maverick, Andrew W.

doi:10.1107/s1600536807018120

Cited by 3 publications

(2 citation statements)

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“…The title compound was described over 100 years ago (Scholtz, 1897;Knoevenagel et al, 1903). We have recently reported the structure of 1,1 0 ,1 00 -[(5R,6R)-6-hydroxy-6-methyltetrahydro-2H-pyran-3,3,5-triyl]triethanone (Burton et al, 2007), which is formed when excess formaldehyde is used in the synthesis. For related literature, see: Allen et al (1998); Wilson (1963).…”

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confidence: 99%

3,5-Diacetylheptane-2,6-dione

2007

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.041; wR factor = 0.113; data-to-parameter ratio = 18.9.The title compound, C 11 H 16 O 4 , was produced when pentane-2,4-dione (acacH) was treated with formaldehyde in a ca 2.16:1 molar ratio. The compound exists in the solid state as the keto tautomer, although the enol tautomer also exists in solution. The C O distances are in the range 1.2097 (18)-1.2169 (18) Å . Intermolecular C OÁ Á ÁC O interactions exist, the shortest having a CÁ Á ÁO distance of 3.378 (2) Å . organic compounds o3108 # 2007 International Union of Crystallography

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Section: Related Literaturementioning

confidence: 99%

3,5-Diacetylheptane-2,6-dione

2007

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“…data reports mation is almost always stabilized (e.g. Burton et al, 2007). Only a few exceptions to this rule are known, for some large molecules with steric hindrance issues (e.g.…”

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(23R,23¹ S,25S)-23¹,26-Epoxy-23-ethylfurost-20(22)-en-3β-ol

Guerrero‐Luna¹,

Hernández-Linares²,

Cárdenas-García³

et al. 2023

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The title compound, C29H46O3, is a steroid synthesized through a rearrangement of a sarsasapogenin derivative in acidic medium. The newly formed ring F is a tetrahydro-2H-pyran heterocycle substituted by two methyl groups placed in equatorial positions. This ring displays a chair conformation, while dihydrofuran ring E, to which it is bonded, has an envelope conformation. The molecules are associated by weak O—H...O hydrogen bonds to form chains running in the [101] direction in the crystal.

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A simple one-pot, multi-component synthesis of cyano-functionalized bis-β-diketones

Urbatsch

Gee

Deacon

et al. 2013

Tetrahedron Letters

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1,1′,1′′-[(5RS,6RS)-6-Hydroxy-6-methyl-3,4,5,6-tetrahydro-2H-pyran-3,3,5-triyl]triethanone

Abstract: In the title compound, C12H18O5, the ring has a chair conformation, with endocyclic torsion angle magnitudes in the range 47.7 (3)–66.7 (2)°. The OH group donates an intermolecular hydrogen bond to a C=O group with an O...O distance of 2.791 (3) Å, forming chains.

Cited by 3 publications

References 3 publications

3,5-Diacetylheptane-2,6-dione

3,5-Diacetylheptane-2,6-dione

(23R,23¹ S,25S)-23¹,26-Epoxy-23-ethylfurost-20(22)-en-3β-ol

A simple one-pot, multi-component synthesis of cyano-functionalized bis-β-diketones

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1,1′,1′′-[(5RS,6RS)-6-Hydroxy-6-methyl-3,4,5,6-tetrahydro-2H-pyran-3,3,5-triyl]triethanone

Abstract: In the title compound, C12H18O5, the ring has a chair conformation, with endocyclic torsion angle magnitudes in the range 47.7 (3)–66.7 (2)°. The OH group donates an intermolecular hydrogen bond to a C=O group with an O...O distance of 2.791 (3) Å, forming chains.

Cited by 3 publications

References 3 publications

3,5-Diacetylheptane-2,6-dione

3,5-Diacetylheptane-2,6-dione

(23R,231 S,25S)-231,26-Epoxy-23-ethylfurost-20(22)-en-3β-ol

A simple one-pot, multi-component synthesis of cyano-functionalized bis-β-diketones

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(23R,23¹ S,25S)-23¹,26-Epoxy-23-ethylfurost-20(22)-en-3β-ol