Methysticin

Base Information

• Chemical Name: Methysticin
• CAS No.: 20697-20-5
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• Mol file: 20697-20-5.mol

Synonyms:5,6-Dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-2H-pyran-2-one;(R-(E))-6-(2-(1,3-Benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one;2H-Pyran-2-one, 6-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, (6R)-;

Chemical Property of Methysticin

Chemical Property:

• Vapor Pressure: 5.39E-10mmHg at 25°C
• Melting Point: 129-131 °C
• Refractive Index: 1.597
• Boiling Point: 496.5 °C at 760 mmHg
• Flash Point: 224 °C
• PSA: 53.99000
• Density: 1.31 g/cm³
• LogP: 2.27430

Purity/Quality:

≥98% ^*data from raw suppliers

Methysticin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DL-Methysticin is a useful synthetic compound.

Technology Process of Methysticin

There total 11 articles about Methysticin 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: 59.0%

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) + 3,4-(methylenedioxy)benzenediazonium tetrafluoroborate (1682-37-7) → (+/-)-methysticin (495-85-2,6581-44-8,20697-20-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium acetate; In benzonitrile; at 100 ℃; for 1h; stereoselective reaction; Microwave irradiation;

DOI:10.1021/ol901416e

Reference yield: 42.0%

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) + 5-iodo-1,3-benzodioxole (5876-51-7) → (+/-)-methysticin (495-85-2,6581-44-8,20697-20-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 - 150 ℃; for 0.0916667h; Microwave irradiation;

DOI:10.1016/j.tetlet.2008.07.102

Reference yield:

(E)-ethyl 7-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-3-oxohept-6-enoate + dimethyl sulfate (77-78-1) → (+/-)-methysticin (495-85-2,6581-44-8,20697-20-5)

Guidance literature:

(E)-ethyl 7-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-3-oxohept-6-enoate; With potassium carbonate; In methanol; at 20 ℃; for 2h;

dimethyl sulfate; In acetone; at 20 ℃; Inert atmosphere;

DOI:10.3998/ark.5550190.0013.813

upstream raw materials:

methyl 4-bromo-3-methoxy-2-butenoate

(E)-3,4-methylenedioxycinnamaldehyde

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one

5-iodo-1,3-benzodioxole

Downstream raw materials:

(+/-)-dihydromethysticin

piperonal

3,4-Dihydroxybenzoic acid

7-benzo[1,3]dioxol-5-yl-3-methoxy-hepta-2,4-dienoic acid