900555

(N-Isocyanoimino)triphenylphosphorane

95%

• Sinónimos: Pinc
• Fórmula empírica (notación de Hill): C₁₉H₁₅N₂P
• Número de CAS: 73789-56-7
• Peso molecular: 302.31
• Número MDL: MFCD09038528
• Código UNSPSC: 12352209
• NACRES: NA.22

Propiedades

• Nivel de calidad: 100
• Análisis: 95%
• formulario: solid
• aplicaciones: peptide synthesis
• InChI: 1S/C19H15N2P/c1-20-21-22(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h2-16H
• Clave InChI: NIDTXBFHPXMXTR-UHFFFAOYSA-N

Descripción

Descripción general

(N-Isocyanoimino)triphenylphosphorane (Pinc) is a bench-stable solid reagent widely used in organic synthesis. It is an amphoteric compound with unique properties that make it a versatile tool for various applications, including heterocycle synthesis and macrocyclization of peptides. Pinc facilitates cyclization and incorporation of a conformational control element into peptide macrocycles, leading to desired drug properties such as improved membrane permeability, lipophilicity, and aqueous solubility. Its ability to form oxadiazoles offers opportunities for the development of new transformations.

Aplicación

As reported by the lab of Andrei Yudin, Pinc enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. It enables the formation of disubstituted 1,3,4-oxadiazoles by intercepting the key mixed anhydride characteristic of the Ugi reaction. Furthermore, the resulting peptide macrocycles containing oxadiazole exhibit improved drug properties such as cell-permeability and a rigid conformation.

Características y beneficios

• Bench-stable solid: Pinc is a stable reagent that can be easily handled and stored.
• Facilitates cyclization and incorporation of conformational control element: Pinc enables the formation of peptide macrocycles with a desired conformation, leading to improved drug properties.
• Amphoteric properties: Pinc′s amphoteric nature allows for the design of new multicomponent reactions, expanding its synthetic capabilities.
• Desired drug properties: The resulting peptide macrocycles exhibit enhanced membrane permeability, lipophilicity, and aqueous solubility, making them desirable for drug development.
• Versatile transformations: Pinc′s ability to form oxadiazoles opens up opportunities for the development of novel synthetic transformations.

Información de seguridad

• Pictogramas: GHS07
• Palabra de señalización: Warning
• Frases de peligro: H315,H319,H335
• Consejos de prudencia: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Clasificaciones de peligro: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Órganos de actuación: Respiratory system
• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable