7-Methoxy-4,4-dimethyl-1,3-isochromandione
[CAS# 55974-25-9]

Identification

• Name: 7-Methoxy-4,4-dimethyl-1,3-isochromandione
• Synonyms: 7-Methoxy-4,4-dimethyl-1H-2-benzopyran-1,3(4H)-dione
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.22
• CAS Registry Number: 55974-25-9
• EC Number: 611-342-0
• SMILES: CC1(C2=C(C=C(C=C2)OC)C(=O)OC1=O)C

Properties

• Density: 1.205±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.528, Calc.^*
• Boiling Point: 366.9±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 164.4±27.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H319-H412
• Precautionary Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

7-Methoxy-4,4-dimethyl-1,3-isochromandione is a structurally unique compound belonging to the class of isochromandiones. This compound features a 1,3-dioxo functionality within the isochroman framework, along with a methoxy group at the 7-position and two methyl groups at the 4-position, contributing to its steric and electronic properties. Its distinct chemical structure has made it an important molecule in medicinal chemistry and synthetic organic chemistry.

The discovery of 7-methoxy-4,4-dimethyl-1,3-isochromandione can be traced to efforts in the mid-20th century to explore derivatives of isochroman for their potential bioactivity. Isochromandiones were of particular interest due to their dual carbonyl functionality, which provided a versatile platform for chemical modifications. The introduction of the methoxy group at the 7-position was aimed at enhancing the compound’s electronic characteristics, while the geminal dimethyl substitution at the 4-position was found to impart significant steric stability, making it more resistant to degradation.

This compound has found applications in the development of pharmacologically active agents, particularly in the areas of anticancer and anti-inflammatory research. The presence of the isochromandione core has been shown to exhibit biological activity through interactions with specific enzymes and receptors. For instance, derivatives of 7-methoxy-4,4-dimethyl-1,3-isochromandione have demonstrated inhibitory effects on certain enzymes involved in cancer cell proliferation, making them potential candidates for antitumor drug development.

In synthetic organic chemistry, this compound is used as a building block for the preparation of more complex molecules. Its reactive carbonyl groups allow for a variety of chemical transformations, including nucleophilic addition and cycloaddition reactions. The methoxy substituent acts as an electron-donating group, influencing reaction pathways and improving the regioselectivity of certain transformations. This versatility has made it a valuable intermediate in the synthesis of natural products and bioactive compounds.

The compound also plays a role in the study of reaction mechanisms. Its well-defined structure has been utilized as a model compound to investigate the behavior of isochroman derivatives under various reaction conditions. These studies have provided insights into the stability and reactivity of similar systems, aiding the design of new synthetic routes and the development of novel materials.

7-Methoxy-4,4-dimethyl-1,3-isochromandione continues to be a subject of research due to its potential applications in drug discovery and chemical synthesis. Its stability, reactivity, and bioactivity highlight its importance as a multifunctional compound in various fields of chemistry and pharmacology.