Dihydro-2H-pyran-3(4H)-one

Base Information

• Chemical Name: Dihydro-2H-pyran-3(4H)-one
• CAS No.: 23462-75-1
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 2932999099
• European Community (EC) Number: 813-813-8
• DSSTox Substance ID: DTXSID40178015
• Nikkaji Number: J113.106K
• Wikidata: Q72506618
• Mol file: 23462-75-1.mol

Synonyms:Dihydro-2H-pyran-3(4H)-one;23462-75-1;oxan-3-one;2H-Pyran-3(4H)-one, dihydro-;Tetrahydropyran-3-one;dihydropyran-3-one;MFCD00182426;3-Tetrahydropyranone;SCHEMBL14653;LEAD(II)ACETYLACETONATE;DTXSID40178015;CS-D1576;BBL101692;STL555488;AKOS006282290;PB27461;SB19934;DS-11715;SY003102;A4918;AM20090251;BB 0260334;FT-0650763;EN300-72286;J-520324;InChI=1/C5H8O2/c6-5-2-1-3-7-4-5/h1-4H

Chemical Property of Dihydro-2H-pyran-3(4H)-one

Chemical Property:

• Vapor Pressure: 1.12mmHg at 25°C
• Refractive Index: 1.44
• Boiling Point: 176 °C at 760 mmHg
• Flash Point: 70.4 °C
• PSA: 26.30000
• Density: 1.065 g/cm³
• LogP: 0.36590
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 78.1

Purity/Quality:

98%, ^*data from raw suppliers

Dihydro-?2H-?pyran-?3(4H)?-?one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1CC(=O)COC1
• Uses: Dihydro-?2H-?pyran-?3(4H)?-?one is a general chemical reagent used in the synthesis of pharmaceuticals such as the preparation of tetrahydropyran-2-yl chromans, a highly selective beta-site amyloid precursor protein cleaving enzyme 1 (BACE) inhibitor.

Technology Process of Dihydro-2H-pyran-3(4H)-one

There total 16 articles about Dihydro-2H-pyran-3(4H)-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: 99.0%

3,3-dimethoxytetrahydro-2H-pyran (1403495-64-6) → 5,6-dihydro-2H-pyran-3(4H)-one (23462-75-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.3998/ark.5550190.0013.820

Reference yield: 90.0%

Oxan-3-ol (19752-84-2) → 5,6-dihydro-2H-pyran-3(4H)-one (23462-75-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2.5h; Molecular sieve;

DOI:10.3987/COM-10-S(E)73

Reference yield: 78.5%

4-(3,4-dihydro-2H-pyran-5-yl)morpholine (82272-05-7) → 5,6-dihydro-2H-pyran-3(4H)-one (23462-75-1)

Guidance literature:

With citric acid; In water; at 10 - 20 ℃; for 7h; Solvent; Temperature; Reagent/catalyst;

upstream raw materials:

Oxan-3-ol

<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, S*)

<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, R*)

2H-pyran-3(6H)-one

Downstream raw materials:

2-amino-4H-1-benzopyran-4-one

(+)-3-hydroxytetrahydropyran

Tetrahydro-pyran-3-ol

5,6-Dihydro-2-(3,4,5-trimethoxybenzyliden)-2H-pyran-3(4H)-on

Refernces

Stereoselective synthesis of donor-acceptor substituted cyclopropafuranones by intramolecular cyclopropanation of vinylogous carbonates: Divergent synthesis of tetrahydrofuran-3-one, tetrahydropyran-3-one, and lactones

10.1021/ol902301h

The research describes a novel and highly stereoselective method for synthesizing donor-acceptor substituted cyclopropafuranones through intramolecular cyclopropanation of vinylogous carbonates using copper catalysts. The purpose of this study is to develop a versatile synthetic strategy for creating a diverse array of structural motifs, including tetrahydrofuran-3-one, tetrahydropyran-3-one, and lactones, by selectively cleaving the cyclopropane bonds in these compounds. The study concludes that the cyclopropafuranones synthesized through this method exhibit remarkable reactivity and selectivity, allowing for the regioselective cleavage of each cyclopropane bond under different reaction conditions. This leads to the formation of a wide range of valuable structural frameworks with potential applications in the synthesis of natural products and related compounds.