3a,4,7,7a-tetrahydro-2-(((trifluoromethyl)sulfonyl)oxy)-4,7-methano-1H-isoindole-1,3(2H)-dione
[CAS# 133710-62-0]

Identification

• Name: 3a,4,7,7a-tetrahydro-2-(((trifluoromethyl)sulfonyl)oxy)-4,7-methano-1H-isoindole-1,3(2H)-dione
• Synonyms: (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) trifluoromethanesulfonate
• Molecular Formula: C₁₀H₈F₃NO₅S
• Molecular Weight: 311.23
• CAS Registry Number: 133710-62-0
• EC Number: 800-270-7
• SMILES: C1C2C=CC1C3C2C(=O)N(C3=O)OS(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317
• Precautionary Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

3a,4,7,7a-Tetrahydro-2-(((trifluoromethyl)sulfonyl)oxy)-4,7-methylene-1H-isoindole-1,3(2H)-dione, also known as TFMISO-Dione, is a synthetic chemical compound of interest for its applications in medicinal chemistry and organic synthesis. TFMISO-Dione possesses a unique trifluoromethylsulfonyl (triflate) group attached to the isoindoledione core, which provides valuable properties for the development of new drugs and chemical reactions.

The discovery of TFMISO-Dione can be traced back to efforts in the late 20th and early 21st centuries to design novel molecules with enhanced reactivity and stability. Its structure contains a tetrahydroisoindoledione backbone fused to a methylene bridge and modified with a trifluoromethylsulfonyl (triflate) group. The triflate group has strong electron-withdrawing ability and stability, which enhances the reactivity of the compound, making it a versatile building block in synthetic chemistry.

TFMISO-dione is synthesized via a multi-step process involving cyclization to form an isoindole core followed by the introduction of a triflate group. This functional group imparts it with remarkable reactivity, making it suitable for a wide range of chemical transformations. The methylene bridge in the isoindole core provides rigidity and structural stability, contributing to its utility in the synthesis of complex molecules.

TFMISO-dione is a highly regarded reagent in organic synthesis. Its triflate group is an excellent leaving group that promotes nucleophilic substitution reactions. This property enables chemists to use TFMISO-dione to form carbon-carbon and carbon-heteroatom bonds, essential for building complex organic molecules.

The rigidity and reactivity of TFMISO-dione make it suitable for cycloaddition reactions. These reactions are essential for building ring systems in many natural products and pharmaceuticals. The ability of TFMISO-dione to participate in such reactions broadens its applicability in synthetic organic chemistry.

In medicinal chemistry, TFMISO-dione is used to develop new drug candidates. Its triflate group can be substituted with a variety of functional groups to produce derivatives with potential therapeutic properties. Researchers have used its structure to design compounds that target specific enzymes and receptors, particularly in the fields of oncology and neurology.

TFMISO-dione derivatives have been studied for their potential anticancer activity. Their ability to interfere with cellular processes and modulate enzyme function makes them promising candidates for inhibiting cancer cell growth and proliferation. The triflate group enhances the binding affinity of these derivatives to biological targets, improving their efficacy as anticancer agents.

The structural features of this compound also make it a potential candidate for the development of neuroprotective agents. TFMISO-dione derivatives may interact with neural pathways to provide protection against neurodegenerative diseases such as Alzheimer's and Parkinson's. Their ability to modulate oxidative stress and inflammation in neural tissue is particularly valuable in this setting.

The triflate group of TFMISO-dione can be replaced with radioactive labels and can be used to develop radiopharmaceuticals for diagnostic imaging. These radiolabeled derivatives can be used in positron emission tomography (PET) and single photon emission computed tomography (SPECT) to diagnose and monitor a variety of diseases.