3,6-dihydro-2H-pyran-2-one

Base Information

• Chemical Name: 3,6-dihydro-2H-pyran-2-one
• CAS No.: 3393-45-1
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID90955515
• Nikkaji Number: J758.964F
• Wikidata: Q72466021
• Mol file: 3393-45-1.mol

Synonyms:3,6-dihydro-2H-pyran-2-one;2,5-dihydropyran-6-one;2H-Pyran-2-one, 3,6-dihydro;pyran-2(6h)-one;DTXSID90955515;CHEBI:182770;VREFDQNWPNDZEX-UHFFFAOYSA-N;EN300-44828964

Chemical Property of 3,6-dihydro-2H-pyran-2-one

Chemical Property:

• Vapor Pressure: 0.055mmHg at 25°C
• Refractive Index: n20/D 1.483(lit.)
• Boiling Point: 233.723 °C at 760 mmHg
• Flash Point: 89.106 °C
• PSA: 26.30000
• Density: 1.12 g/cm³
• LogP: 0.48950
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 105

Purity/Quality:

97%min ^*data from raw suppliers

5,6-Dihydro-2H-pyran-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.
• Hazard Codes: R10:Flammable.
• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C=CCOC1=O
• General Description: 5,6-Dihydro-2H-pyran-2-one, also known as 2-pentenolide or dihydro-α-pyrone, is a lactone featuring a six-membered ring with an unsaturated carbonyl group. This structural motif is prevalent in biologically active natural products, and its enantiopure form, such as (6R)-5,6-dihydro-2H-pyran-2-one, can be synthesized chemoenzymatically through multi-step processes involving enzymatic dioxygenation, microwave-assisted reactions, and tin-mediated lactonization. The compound serves as a versatile intermediate for the preparation of various pharmacologically relevant molecules.

Technology Process of 3,6-dihydro-2H-pyran-2-one

There total 2 articles about 3,6-dihydro-2H-pyran-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(E)-N-benzyl-N-(but-3-en-1-yl)cinnamamide + phenylacetylene (536-74-3) → 5,6-dihydro-pyran-2-one (3393-45-1) + (8SR,8aSR)-2-benzyl-6,8-diphenyl-3,4,4a,7,8,8a-hexahydroisoquinolin-1(2H)-one + (8SR,8aRS)-2-benzyl-6,8-diphenyl-3,4,4a,7,8,8a-hexahydroisoquinolin-1(2H)-one + N-benzyl-N-[(Z)-5-phenylhexa-3,5-dien-1-yl]cinnamamide

Guidance literature:

With [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In toluene; at 90 ℃; for 48h; Overall yield = 78 %; diastereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.3762/bjoc.11.161

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 5,6-dihydro-pyran-2-one (3393-45-1) + 6-(3-phenylpropyl)-2H-pyran-4(3H)-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: tert.-butylhydroperoxide; sodium acetate; dirhodium tetrakis(caprolactamate); oxygen / water; dichloromethane / 20 °C

With tert.-butylhydroperoxide; dirhodium tetrakis(caprolactamate); tert.-butyl lithium; oxygen; sodium acetate; In tetrahydrofuran; dichloromethane; water; pentane;

DOI:10.1021/acs.joc.7b01163

Reference yield: 100.0%

5,6-dihydro-pyran-2-one (3393-45-1) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9)

Guidance literature:

With hydrogen; palladium(II) complex of ferrocenylamine sulfide ⁽¹⁾; In acetone; for 10h; under 4137.2 Torr;

DOI:10.1016/0040-4039(91)80065-E

upstream raw materials:

phenylacetylene

3,4-dihydro-2H-pyran

Downstream raw materials:

methyl tetrahydro-2-methoxyfuran-2-carboxylate

trans-2-(3,3-dimethylallyl)-3--3,4,5,6-tetrahydropyran-2-one

(2-Oxo-tetrahydro-pyran-4-yl)-phosphonic acid dimethyl ester

trans-3-(2-methyl-2-propenyl)-4--3,4,5,6-tetrahydropyran-2-one

Refernces

Chemoenzymatic preparation of (6R)-5,6-dihydro-2H-pyran-2-one: A ubiquitous structural motif of biologically active lactones

10.1016/j.tetasy.2013.10.005

The research presents a chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one, a structural motif found in numerous biologically active lactones. The synthesis starts with bromobenzene and involves key steps such as enzymatic dioxygenation using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin-mediated lactonization. The stereochemical assignment of the alcohol is confirmed by NMR analysis of Mosher's derivatives. The synthesis consists of 14 steps with an overall yield of 11%, and the resulting (6R)-5,6-dihydro-2H-pyran-2-one can be used for the preparation of various biologically active natural products.