(Isocyanoimino)triphenylphosphorane

• CAS: 73789-56-7
• Catalog Number: ACM73789567
• Category: Main Products
• Molecular Weight: 302.309561
• Molecular Formula: C₁₉H₁₅N₂P
• Synonyms: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE;Nsc371099
• IUPAC Name: isocyanoimino(triphenyl)-$l^{5}-phosphane
• SMILES: [C-]#[N+]N=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• InChI Key: NIDTXBFHPXMXTR-UHFFFAOYSA-N
• Exact Mass: 302.09700

Case Study

(Isocyanoimino)triphenylphosphorane as a Key Mediator for Conformationally-Guided Peptide Macrocyclization

Diaz, Diego B., et al. The Journal of Organic Chemistry 89.3 (2024): 1483-1491.

(Isocyanoimino)triphenylphosphorane (Pinc) acts as a dual-function activator that both chemically activates the peptide termini and enforces a favorable spatial arrangement that promotes intramolecular cyclization. In practice, it forms an activated phosphonium-ylide/iminum-type intermediate that shepherds the carboxylate into the peptide interior and aligns the reacting partners, decreasing the likelihood of intermolecular reactions and enabling ring closure under milder, less dilute conditions.
Mechanistic Insight
· Stereochemical bias: Reactions driven by Pinc often display moderate diastereoselectivity consistent with a Si-face preference for addition of the isocyanide to an E-iminium intermediate; the local stereochemistry of adjacent residues (e.g., an l-proline amide) influences the facial selectivity.
· Noncovalent assistance: The phosphonium-ylide intermediate generated from Pinc engages the linear peptide in a way that resembles a transient intramolecular "ion-pairing" or attractive interaction, effectively preorganizing the chain and enclosing the terminal carboxylate inside the nascent macrocycle. This reduces entropic penalties and suppresses competing intermolecular pathways.
· For shorter or structurally modified peptides, Pinc's mechanism adapts-nucleophilic heterocycles such as thiazole or imidazole can intercept nitrilium intermediates, redirecting the cyclization pathway and enabling diverse cyclic scaffold formation.

(Isocyanoimino)Triphenylphosphorane for Rapid Three-Component Assembly of 4H-Furo[3,2-C]Pyran-4-Ones

Adib, Mehdi, et al. Helvetica Chimica Acta 96.4 (2013): 675-681.

Fused O,O-heterocycles of the furo[3,2-c]pyran family are prominent scaffolds in natural products and bioactive molecules. Mild methods that allow for the easy assembly of this structural motif with a wide variety of substituents installed would be of utility in medicinal-chemistry and natural-product analog development programs. Herein, this work described the use of (isocyanoimino)triphenylphosphorane (compound 1) as a key precursor in a simple, high-yielding synthesis of functionalized furo[3,2-c]pyran derivatives.
Synthetic Procedure: A typical procedure would combine one equivalent each of (isocyanoimino)triphenylphosphorane, an aryl aldehyde and 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione (dehydroacetic acid) in dichloromethane, which was stirred at approximately 25 °C. Conversion to the target 4H-furo[3,2-c]pyran-4-one products is complete within about four hours. Products that precipitate from the reaction may be isolated by filtration and washing; where no solid forms, simple evaporation and silica chromatography afford the pure material. A variety of aryl substituents were demonstrated, including nitro, fluoro, chloro and methoxy derivatives.
The three-component sequence furnished the desired 2-(arylmethylidenehydrazinylidene)-3-hydroxy-4H-furo[3,2-c]pyran-4-ones in excellent yields (85-94%) across the scope tested. Representative isolated yields reported include 94% for the 4-nitro derivative and 90-93% for 4-fluoro, 3-chloro and 3-methoxy examples.

Custom Q&A

What is the molecular formula of (Isocyanoimino)triphenylphosphorane?

The molecular formula is C19H15N2P.

What is the molecular weight of (Isocyanoimino)triphenylphosphorane?

The molecular weight is 302.3 g/mol.

What is the IUPAC name of (Isocyanoimino)triphenylphosphorane?

The IUPAC name is isocyanoimino(triphenyl)-λ5-phosphane.

What is the CAS number for (Isocyanoimino)triphenylphosphorane?

The CAS number is 73789-56-7.

How many hydrogen bond acceptors are there in (Isocyanoimino)triphenylphosphorane?

There are 2 hydrogen bond acceptors.

How many rotatable bond counts are there in (Isocyanoimino)triphenylphosphorane?

There are 3 rotatable bond counts.

What is the topological polar surface area of (Isocyanoimino)triphenylphosphorane?

The topological polar surface area is 16.7Ų.

How many heavy atoms are there in (Isocyanoimino)triphenylphosphorane?

There are 22 heavy atoms.

Is (Isocyanoimino)triphenylphosphorane a canonicalized compound?

Yes, (Isocyanoimino)triphenylphosphorane is a canonicalized compound.

What is the InChIKey of (Isocyanoimino)triphenylphosphorane?

The InChIKey is NIDTXBFHPXMXTR-UHFFFAOYSA-N.