1,3,4,6-Tetrakis(methoxymethyl)-3a-methyl-6a-propyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
[CAS 220140-29-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1,3,4,6-Tetrakis(methoxymethyl)-3a-methyl-6a-propyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
• Molecular Formula: C₁₆H₃₀N₄O₆
• Molecular Weight: 374.43
• CAS Registry Number: 220140-29-4
• EC Number: 682-847-1
• SMILES: CCCC12C(N(C(=O)N1COC)COC)(N(C(=O)N2COC)COC)C

Discovery and Applications

1,3,4,6-Tetrakis(methoxymethyl)-3a-methyl-6a-propyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is a highly substituted, fused heterocyclic compound featuring an imidazo[4,5-d]imidazole core. Its structure combines a bicyclic urea-like framework with multiple **methoxymethyl (MOM) ether** substituents, along with alkyl groups that influence steric and electronic properties. This type of molecule is typically encountered as a protected intermediate in complex organic synthesis.

The molecular structure consists of a fused bicyclic system formed by two imidazole-derived rings, incorporating two carbonyl groups at the 2- and 5-positions (a diimide or cyclic urea motif). The “tetrahydro” designation indicates partial saturation of the ring system, reducing aromaticity and increasing conformational flexibility. Substituents include four methoxymethyl groups attached to nitrogen atoms (N-MOM protection), as well as a methyl group at the 3a-position and a propyl group at the 6a-position. These substituents create a sterically crowded environment and enhance solubility in organic media.

The methoxymethyl groups serve primarily as **protecting groups** for nitrogen atoms. They stabilize the heterocycle during multistep synthesis by preventing unwanted side reactions such as alkylation or acylation at the nitrogen sites. These protecting groups can later be removed under acidic conditions to regenerate the free imide or amine functionalities.

Synthesis of this compound generally involves construction of the fused imidazoimidazole core from urea or diamine precursors, followed by stepwise N-alkylation using methoxymethyl halides to introduce the MOM groups. The alkyl substituents at the bridgehead positions (3a and 6a) are introduced earlier in the synthesis to control stereochemistry and reactivity. Reaction conditions must be carefully controlled to avoid over-alkylation or decomposition of the sensitive heterocyclic framework.

Compounds of this type are mainly used as **synthetic intermediates** in medicinal chemistry or heterocyclic chemistry. The protected nitrogen atoms allow selective functionalization elsewhere in the molecule, enabling the stepwise construction of more complex bioactive structures. After deprotection, the resulting imidazole-containing frameworks can exhibit biological activity or serve as ligands, enzyme inhibitors, or building blocks for pharmaceuticals.

In addition, the rigid bicyclic structure and multiple heteroatoms make such compounds of interest in coordination chemistry and materials research, where they can interact with metal ions or participate in hydrogen-bonding networks.

Overall, 1,3,4,6-tetrakis(methoxymethyl)-3a-methyl-6a-propyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is a complex, highly functionalized heterocycle. Its combination of a protected imidazoimidazole core, multiple MOM groups, and alkyl substituents makes it a useful intermediate for the controlled synthesis of advanced heterocyclic and potentially bioactive compounds.

References

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