Nectriapyrone

Base Information

• Chemical Name: Nectriapyrone
• CAS No.: 57685-79-7
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• NSC Number: 263671
• Nikkaji Number: J12.717E
• Wikidata: Q74418262
• Mol file: 57685-79-7.mol

Synonyms:NECTRIAPYRONE;57685-79-7;6-[(E)-but-2-en-2-yl]-4-methoxy-3-methylpyran-2-one;6-((E)-But-2-en-2-yl)-4-methoxy-3-methylpyran-2-one;4-Methoxy-3-methyl-6-[(E)-1-methyl-1-propenyl]-2H-pyran-2-one;NSC263671;NRLCQITWKJENAT-FNORWQNLSA-;CHEBI:142639;AKOS040734712;NSC 263671;NSC-263671;6-[(2E)-but-2-en-2-yl]-4-methoxy-3-methyl-2H-pyran-2-one;InChI=1/C11H14O3/c1-5-7(2)9-6-10(13-4)8(3)11(12)14-9/h5-6H,1-4H3/b7-5+

Chemical Property of Nectriapyrone

Chemical Property:

• Vapor Pressure: 7.42E-05mmHg at 25°C
• Boiling Point: 342.7°C at 760 mmHg
• Flash Point: 142°C
• PSA: 39.44000
• Density: 1.07g/cm³
• LogP: 2.38000
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C1=CC(=C(C(=O)O1)C)OC
• Isomeric SMILES: C/C=C(\C)/C1=CC(=C(C(=O)O1)C)OC

Technology Process of Nectriapyrone

There total 18 articles about Nectriapyrone 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: 91.0%

3-methyl-4-hydroxy-6-(1-methyl-trans-1-propenyl)-2-pyrone (78440-88-7) + dimethyl sulfate (77-78-1) → nectriapyrone (57685-79-7)

Guidance literature:

With potassium carbonate; In acetone; at 70 ℃; for 3.5h;

DOI:10.1002/ejoc.201800621

Reference yield: 57.0%

ethyltriphenylphosphonium bromide (1530-32-1) + 6-acetyl-4-methoxy-3-methyl-2H-pyran-2-one (140866-24-6) → nectriapyrone (57685-79-7) + (Z)-6-(but-2-en-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one (1393595-89-5)

Guidance literature:

ethyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

6-acetyl-4-methoxy-3-methyl-2H-pyran-2-one; In tetrahydrofuran; hexane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2012.06.104

Reference yield:

3-methyl-4-hydroxy-6-(1-methyl-trans-1-propenyl)-2-pyrone-5-carboxylic acid (78440-87-6) → nectriapyrone (57685-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / quinoline / 0.25 h / 210 - 220 °C

2: 106 mg / diethyl ether / 24 h / Ambient temperature

In quinoline; diethyl ether;

DOI:10.1002/jhet.5570180227

upstream raw materials:

6-(1-hydroxyethyl)-4-methoxy-3-methyl-2H-pyran-2-one

ethyltriphenylphosphonium bromide

6-acetyl-4-methoxy-3-methyl-2H-pyran-2-one

3,5-heptanedione

Refernces

• 1、 Burkhardt, Immo,Dickschat, Jeroen S.. "Synthesis and Absolute Configuration of Natural 2-Pyrones". . p. 3144 - 3157. Retrieved 2018/07/06.
• 2、 Abramson,Wormser. "Synthesis of nectriapyrone". . p. 363 - 366. Retrieved 2007/10/02.