6-METHYL-3,5-HEPTADIEN-2-ONE

Base Information

• Chemical Name: 6-METHYL-3,5-HEPTADIEN-2-ONE
• CAS No.: 1604-28-0
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.183
• Hs Code.: 29141900
• European Community (EC) Number: 216-507-7,865-146-7
• UNII: P7CMP2E76C
• Nikkaji Number: J195.217J,J435.355B,J100.508A
• Metabolomics Workbench ID: 5444
• Mol file: 1604-28-0.mol

Synonyms:2-Methyl-2,4-heptadien-6-one;6-Methylhepta-3,5-dien-2-one;6-Methylhepta-3,5-diene-2-one;

Chemical Property of 6-METHYL-3,5-HEPTADIEN-2-ONE

Chemical Property:

• Vapor Pressure: 0.464mmHg at 25°C
• Refractive Index: 1.5340
• Boiling Point: 193.45 °C at 760 mmHg
• Flash Point: 68.582 °C
• PSA: 17.07000
• Density: 0.858 g/cm³
• LogP: 2.09780
• Water Solubility.: Miscible with alcohol. Immiscible with water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 124.088815002
• Heavy Atom Count: 9
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

6-Methylhepta-3,5-dien-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R36/38:Irritating to eyes and skin.
• Hazard Codes: Xi
• Statements: 10-36/38-36/37/38
• Safety Statements: 26-36-36/37-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=CC(=O)C)C
• Isomeric SMILES: CC(=C/C=C/C(=O)C)C
• Description: 6-Methyl-3,5-heptadien-2-one has a cinnamon-like odor with a coconut undertone. May be prepared by reacting 2-methylbuten- 2-al with acetone in the presence of sodium ethylate or sodium hydroxide; by pyrolysis of tertiary actylenic carbinyl acetoacetates in the presence of an acid catalyst.
• Uses: 6-Methyl-3,5-heptadien-2-one is used in the preparation of (RS)-(E)-2,6-dimethyl-1,2-epoxy-3,5-heptadiene.

Technology Process of 6-METHYL-3,5-HEPTADIEN-2-ONE

There total 17 articles about 6-METHYL-3,5-HEPTADIEN-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: 2.0%

3,3-dimethyl acrylaldehyde (107-86-8) + ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate (13148-05-5) → 6-methylhepta-3,5-dien-2-one (16647-04-4,29178-96-9,1604-28-0) + 1E ethyl 2,2-dimethyl-6-(4-methylpenta-1,3-dienyl)-2H-pyran-5-carboxylate (114114-79-3) + 1E diethyl 4-(4-methylpenta-1,3-dienyl)-2-(2-methylprop-1-enyl)-6-oxocyclohex-4-ene-1,3-dicarboxylate + (1E) diethyl 4-hydroxy-6-(4-methylpenta-1,3-dienyl)-2-(2-methylprop-1-enyl)cyclohexa-3,5-diene-1,3-dicarboxylate

Guidance literature:

With magnesium sulfate; hydroquinone; for 7h; Further byproducts given; Heating;

Reference yield: 1.0%

ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate (13148-05-5) + 1E ethyl 2,2-dimethyl-6-(4-methylpenta-1,3-dienyl)-2H-pyran-5-carboxylate (114114-79-3) → 6-methylhepta-3,5-dien-2-one (16647-04-4,29178-96-9,1604-28-0) + 4E ethyl 7-methyl-3-oxoocta-4,6-dienoate (111949-23-6) + 1E diethyl 4-(4-methylpenta-1,3-dienyl)-2-(2-methylprop-1-enyl)-6-oxocyclohex-4-ene-1,3-dicarboxylate + (1E) diethyl 4-hydroxy-6-(4-methylpenta-1,3-dienyl)-2-(2-methylprop-1-enyl)cyclohexa-3,5-diene-1,3-dicarboxylate

Guidance literature:

at 130 ℃; for 3h;

Reference yield:

2-methyl-but-3-yn-2-ol (115-19-5) → 1-methyl-4-isopropenylbenzene (1195-32-0) + 3,3-dimethyl acrylaldehyde (107-86-8) + 6-methylhepta-3,5-dien-2-one (16647-04-4,29178-96-9,1604-28-0) + p-cymene-8-ol (1197-01-9) + 4,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde (41793-01-5)

Guidance literature:

polyvanadioorganosiloxane (3.1percent V); In xylene; at 150 - 160 ℃; for 6h; Mechanism; Rate constant; Product distribution;

upstream raw materials:

4-methyleneoxetan-2-one

2-methyl-but-3-yn-2-ol

1-diethylamino-1-buten-3-one

2-methylpropen-1-ylmagnesium bromide

Downstream raw materials:

6-Methyl-3,5-heptadien-2-on-<2,4-dinitrophenylhydrazon>

2-Methyl-hepten-(4)-ol-(6)

rac-trans-1-(-2-(2-methylprop-1-enyl)cyclopropyl)ethanone

4-(dimethyl(phenyl)silyl)-6-methylhept-5-en-2-one

Refernces

• 1、 -. "Method for synthesizing alpha,gamma-unsaturated dienone from propargyl alcohol and catalyst system used for method". Paragraph 0069; 0070; 0072. . Retrieved 2019/04/10.
• 2、 Zou, Yue,Garayalde, David,Wang, Quanrui,Nevado, Cristina,Goeke, Andreas,Ito, Yoshihiko. "Gold-catalyzed cycloisomerization of cyclopropyl alkynyl acetates: A versatile approach to 5-, 6-, and 7-membered carbocycles". supporting information; experimental part. p. 10110 - 10113. Retrieved 2009/05/30.