Cas no 1093759-49-9 (1-Triisopropylsilanyl-7-azaindole)

1-Triisopropylsilanyl-7-azaindole is a protected derivative of 7-azaindole, featuring a triisopropylsilyl (TIPS) group at the 1-position. This modification enhances the compound's stability, making it suitable for use in sensitive synthetic applications, particularly in medicinal chemistry and heterocyclic synthesis. The TIPS group serves as a robust protecting group, shielding the nitrogen atom from undesired reactions while allowing selective functionalization at other positions. Its lipophilic nature also improves solubility in organic solvents, facilitating handling in cross-coupling and metal-catalyzed reactions. This compound is valuable for constructing complex nitrogen-containing scaffolds, offering controlled reactivity and compatibility with a range of reaction conditions.
1-Triisopropylsilanyl-7-azaindole structure
1093759-49-9 structure
Product Name:1-Triisopropylsilanyl-7-azaindole
CAS No:1093759-49-9
MF:C16H26N2Si
MW:274.476544857025
MDL:MFCD09743456
CID:2867563
PubChem ID:49758865
Update Time:2025-05-04

1-Triisopropylsilanyl-7-azaindole Chemical and Physical Properties

Names and Identifiers

    • 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine
    • 1-[Tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine
    • 1-triisopropylsilanyl-7-azaindole
    • AKOS037650723
    • 1-(triisopropylsilyl)pyrrolo[2,3-b]pyridine
    • MFCD09743456
    • DTXSID501210170
    • tri(propan-2-yl)-pyrrolo[2,3-b]pyridin-1-ylsilane
    • CS-B1405
    • CS-15221
    • 1093759-49-9
    • C13180
    • C16H26N2Si
    • SCHEMBL1883096
    • 1-Triisopropylsilanyl-7-azaindole
    • MDL: MFCD09743456
    • Inchi: 1S/C16H26N2Si/c1-12(2)19(13(3)4,14(5)6)18-11-9-15-8-7-10-17-16(15)18/h7-14H,1-6H3
    • InChI Key: DDESQHZPBHAOPS-UHFFFAOYSA-N
    • SMILES: [Si](C(C)C)(C(C)C)(C(C)C)N1C=CC2=CC=CN=C12

Computed Properties

  • Exact Mass: 274.18700
  • Monoisotopic Mass: 274.186525372g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 4
  • Complexity: 279
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 17.8

Experimental Properties

  • PSA: 17.82000
  • LogP: 5.05990

1-Triisopropylsilanyl-7-azaindole Pricemore >>

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Additional information on 1-Triisopropylsilanyl-7-azaindole

Introduction to 1-Triisopropylsilanyl-7-azaindole (CAS No. 1093759-49-9)

1-Triisopropylsilanyl-7-azaindole (CAS No. 1093759-49-9) is a versatile compound that has garnered significant attention in the fields of organic synthesis and medicinal chemistry. This compound, also known as TIPS-protected 7-azaindole, is a valuable intermediate in the synthesis of various bioactive molecules and pharmaceuticals. Its unique structure, characterized by the triisopropylsilyl (TIPS) protecting group and the 7-azaindole core, makes it an essential building block for a wide range of applications.

The triisopropylsilyl (TIPS) protecting group is particularly advantageous due to its stability under a variety of reaction conditions and its ease of removal. This feature allows for the selective protection and deprotection of functional groups, which is crucial in multi-step synthetic processes. The TIPS group can be readily removed using mild acidic conditions, such as TFA (trifluoroacetic acid), without affecting other sensitive functionalities in the molecule.

The 7-azaindole core, on the other hand, is a nitrogen-containing heterocycle that closely resembles the indole scaffold found in many natural products and bioactive compounds. This structural similarity has led to extensive research into the biological activities of 7-azaindole derivatives. Studies have shown that these compounds exhibit a range of pharmacological properties, including anti-inflammatory, antiviral, and anticancer activities.

Recent advancements in the synthesis and application of 1-Triisopropylsilanyl-7-azaindole have further highlighted its potential in drug discovery and development. For instance, a study published in the Journal of Medicinal Chemistry reported the use of this compound as a key intermediate in the synthesis of novel inhibitors targeting specific enzymes involved in cancer progression. The researchers demonstrated that these inhibitors exhibited potent antiproliferative effects against various cancer cell lines, suggesting their potential as therapeutic agents.

In another notable study, scientists explored the use of TIPS-protected 7-azaindole in the development of new antiviral agents. The team synthesized a series of derivatives and evaluated their efficacy against several viral strains, including influenza and herpes simplex virus (HSV). The results showed that certain derivatives displayed significant antiviral activity, making them promising candidates for further preclinical evaluation.

The versatility of 1-Triisopropylsilanyl-7-azaindole extends beyond its use as an intermediate in drug synthesis. It has also found applications in materials science and catalysis. For example, researchers have utilized this compound as a ligand in transition metal-catalyzed reactions, demonstrating its ability to enhance catalytic activity and selectivity. Additionally, its unique electronic properties make it suitable for use in organic electronic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs).

In conclusion, 1-Triisopropylsilanyl-7-azaindole (CAS No. 1093759-49-9) is a highly valuable compound with a wide range of applications in organic synthesis, medicinal chemistry, materials science, and catalysis. Its unique combination of the TIPS protecting group and the 7-azaindole core provides researchers with a powerful tool for developing new bioactive molecules and advanced materials. As ongoing research continues to uncover new properties and applications, this compound is likely to play an increasingly important role in various scientific disciplines.

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