63184-86-1

Basic information

• Product Name: 1,3-Cyclohexanedione, 2,4,4-trimethyl-
• CAS NO: 63184-86-1
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Mol File: 63184-86-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-Cyclohexanedione, 2,4,4-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexanedione, 2,4,4-trimethyl-(63184-86-1)
• EPA Substance Registry System: 1,3-Cyclohexanedione, 2,4,4-trimethyl-(63184-86-1)

Safety Data

• Hazardous Substances Data: 63184-86-1(Hazardous Substances Data)

Usage

Chemical structure

Cyclic ketone with two carbonyl groups and three methyl substituents

Explanation

The compound has a ring structure with two carbonyl (C=O) groups and three methyl (CH3) groups attached at different positions on the ring.

Explanation

The functional groups are the specific parts of the molecule that determine its chemical reactivity and properties. In this case, the carbonyl groups are responsible for the ketone character, and the methyl groups are the substituents.

Explanation

Due to its unique structure, 1,3-Cyclohexanedione, 2,4,4-trimethylis used as a starting material or intermediate in the synthesis of various organic compounds.

Explanation

The compound is utilized in the creation of various products, including fragrances, flavors, and pharmaceuticals, due to its chemical properties and reactivity.

Explanation

1,3-Cyclohexanedione, 2,4,4-trimethylis classified as a hazardous substance, which means it can pose risks to human health and the environment if not handled properly.

Explanation

Due to its hazardous nature, it is essential to follow safety protocols and handle the compound with caution to minimize the risk of exposure and potential harm.

Explanation

The compound is known for its strong odor, which can be a useful identifier but also a potential hazard if inhaled in large quantities.

Functional groups

Carbonyl (C=O) and methyl (CH3) groups

Application

Building block in organic synthesis

Usage

Production of fragrances, flavors, and pharmaceuticals

Hazardous substance

Potential health and environmental risks

Precaution

Handle with care

Strong odor

Characteristic feature

Upstream product

• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 562-46-9 4,4-dimethylcyclohexane-1,3-dione 
• 74-88-4 methyl iodide 
• 1629-58-9 4-penten-3-one 
• 60068-02-2 2,6,6-Trimethyl-3-isobutoxycyclohex-2-en-1-one 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 909530-06-9 2,4,4-trimethyl-3-(3-phenylpropyl)cyclohexen-2-ol 
• 909530-03-6 2,4,4-trimethyl-3-(3-phenylpropyl)cyclohex-2-enone 
• 909530-02-5 2,6,6-trimethyl-1-(3-phenylpropyl)cyclohex-2-enol 
• 565-69-5 ethyl isopropyl ketone 
• 292638-85-8 acrylic acid methyl ester 
• 1663-39-4 tert-Butyl acrylate 
• 64095-45-0 2,2-dimethyl-5-oxo-heptanoic acid methyl ester 

Downstream Products

• 909530-03-6 2,4,4-trimethyl-3-(3-phenylpropyl)cyclohex-2-enone 
• 909530-06-9 2,4,4-trimethyl-3-(3-phenylpropyl)cyclohexen-2-ol 
• 909530-07-0 1,5,5-trimethyl-6-(3-phenylpropyl)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 174910-90-8 3-methoxy-2,6,6-trimethylcyclohex-2-en-1-one 
• 2230-70-8 2,4,4-trimethyl-cyclohexanone 
• 63184-93-0 (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide 
• 79749-53-4 3-((1Z,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-2,4,4-trimethyl-cyclohex-2-enone 
• 72008-26-5 (2E,4Z)-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-1-hydroxy-2,4-pentadiene 
• 63184-87-2 5-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methyl-2-trans-penten-4-yn-1-ol 
• 514-78-3 canthaxanthin 

Relevant articles and documents

Domino Michael-aldol annulations for the stereocontrolled synthesis of bicyclo[3.3.1]nonane and bicyclo[3.2.1]octane derivatives

Domino Michael-aldol annulation of cycloalkane-1,3-diones with enals affords a general route to 6-hydroxybicyclo[3.3.1]nonane-2,9-diones and 2-hydroxybicyclo[3.2.1]octane-6,8-diones, notably in one-pot procedures under convenient conditions. The annulation is shown to be compatible with one or more substituents at six positions of the bicyclo[3.3.1]nonane-2,9-dione scaffold. In some cases, the relative configuration of the product can be controlled by the appropriate choice of solvent, base and temperature for the annulation. In contrast to the chair-chair conformations usually adopted, the bicyclo compounds derived from 2,4,4-trimethylcyclohexane-1,3-dione possessed boat-chair conformations. Oxidation of the annulation products gave the corresponding bicyclo triketones.

Revisiting [3 + 3] route to 1,3-cyclohexanedione frameworks: Hidden aspect of thermodynamically controlled enolates

We have revisited the traditional consecutive Michael-Claisen [3 + 3] process (MC-[3+3]) promising the synthesis of a cyclohexane-1,3-dione derivatives from nonactivated simple ketones and enoates and evaluated its potential in modern organic synthesis. Twenty to thirty examples were demonstrated to be effective. The reactions exhibited remarkable regioselectivity with the Michael addition proceeding through nucleophilic attack by the more hindered site of the ketones without exception. The subsequent Claisen condensation resulted in the formation of carbon-carbon bonds between less hindered site of the ketones and acyl carbon of the enoates. The MC-[3+3] process described is useful for the synthesis of Taxol A-ring synthons in multigram quantities and for the synthesis of other six-membered carbocyclic compounds. A number of control experiments have been conducted to provide strong support for the mechanism of this MC-[3+3].

Canthaxanthin. A new total synthesis

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