29943-42-8 Usage
Description
Tetrahydro-4H-pyran-4-one is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions. Tetrahydro-4H-pyran-4-one is employed in the preparation of 4-methoxytetrahydropyran-4-yl protecting group, synthesis of symmetric tetra substituted methanes.The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran. Tetrahydro-4H-pyran-4-one is also employed in a study of the enantioselective alpha-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid. It undergoes condensation reactions in the preparation of dipeptides and spiroimidazolones. Tetrahydro-4H-pyran-4-one is also employed in wittig reactions for the synthesis of Penicillins and in a ring of vitamin D3.
Application
Tetrahydro-4-pyrone is used in organic synthesis as a building block for more complex chemical structures because it participates in a variety of cycloaddition reactions. Tetrahydro-4H-pyran-4-one is employed in a study of the enantioselective alpha-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid and it undergoes condensation reactions in the preparation of dipeptides and spiroimidazolones. Tetrahydro-4H-pyran-4-one is also employed in wittig reactions for the synthesis of penicillins and in a ring of vitamin D3. Additionally, tetrahydro-4-pyrone is used as solvents in some reactions.
Chemical Properties
colorless to light yellow liquid
Uses
Tetrahydro-4-pyrone is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions.
Purification Methods
Purify the pyrone by repeated distillation, preferably in a vacuum. [Baker J Chem Soc 296 1944, IR: Olsen & Bredoch Chem Ber 91 1589 1958.] The oxime has m 87-88o and b 110-111o/13mm [Cornubert et al. Bull Soc Chim Fr 36 1950]. The 4-nitrophenylhydrazone forms orange-brown needles from EtOH, m 186o [Cawley & Plant J Chem Soc 1214 1938]. [Beilstein 17 I 131, 17 II 287, 17 III/IV 4171, 17/9 V 21.]
Check Digit Verification of cas no
The CAS Registry Mumber 29943-42-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,9,4 and 3 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 29943-42:
(7*2)+(6*9)+(5*9)+(4*4)+(3*3)+(2*4)+(1*2)=148
148 % 10 = 8
So 29943-42-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c6-5-1-3-7-4-2-5/h1-4H2
29943-42-8Relevant articles and documents
Tetrahydro-4 H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture
Bergraser, Julie,Berranger, Thierry,Carlier, Agathe,Delacroix, Kenny,Echeverria, Pierre-Georges,Petit, Laurent,Zahim, Sara
supporting information, (2022/01/12)
This study describes our recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using the commercially available starting materials. The route scouting work and the full development of an efficient access to the target are described. This work culminated in the preparation of above 20 kg of the title compound in our pilot plant facility.
Tetrahydropyranone preparation method
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Paragraph 0017; 0022, (2018/10/11)
The invention relates to a tetrahydropyranone preparation method, the method takes acetone and diethyl oxalate as raw materials, through steps of a ring closure reaction, a decarboxylation reaction, and a reduction reaction, three-step high-yield synthesis is realized to obtain tetrahydropyranone. The tetrahydropyranone preparation method has the advantages of high yield, low cost, and easy operation, and is suitable for industrial preparation method.
Synthesis of azasilacyclopentenes and silanols: Via Huisgen cycloaddition-initiated C-H bond insertion cascades
Shih, Jiun-Le,Jansone-Popova, Santa,Huynh, Christopher,May, Jeremy A.
, p. 7132 - 7137 (2017/10/05)
An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C-H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C-H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.
