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HS Code |
427400 |
| Iupac Name | N-(2-Bromo-3-oxospiro[3.5]non-1-en-1-yl)-4-(2,7-naphthid-1-ylamino)-L-phenylalanine |
| Molecular Formula | C28H25BrN2O3 |
| Molecular Weight | 517.42 g/mol |
| Appearance | Solid (assumed, based on structure) |
| Smiles | C1CCC2(CC1)C(=O)C=C2N(C3=CC=CC4=C3C=CC=N4)C(=O)CC(C5=CC=C(C=C5)N)N |
| Inchi | InChI=1S/C28H25BrN2O3/c29-25-18-24(32)17-27(19-9-4-1-5-10-19)40-28(25)31-26(33)16-22(30)20-11-13-23(14-12-20)34-21-7-2-3-8-15(21)6-7/h2-3,7-8,11-14,18,22H,1,4-6,9-10,16-17,30H2,(H,31,33)/t22-/m0/s1 |
| Storage Conditions | Store at room temperature, away from moisture |
| Usage | Research chemical (potential pharmaceutical intermediate) |
| Synonyms | None reported |
As an accredited N-(2-Bromo-3-Oxospiro[3.5]Non-1-En-1-Yl)-4-(2,7-Naphthid-1-Ylamino)-L-Phenylalanine factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
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Innovation rarely happens in the comfort zone. Years of research and development in structural chemistry have led us to complex molecules that look intimidating on paper yet open doors in the lab. Among these, N-(2-Bromo-3-Oxospiro[3.5]Non-1-En-1-Yl)-4-(2,7-Naphthid-1-Ylamino)-L-Phenylalanine stands out as a tangible example of targeted design with purpose. The name feels like a tongue-twister at first glance, but dig a little deeper and the significance becomes clear for anyone following advances in pharmaceutical intermediates, molecular probes, or synthetic study models.
Over the past decade, chemists have shifted from bulk modifications to precise molecular design. One reason for this comes from the need to explore highly selective reaction pathways and develop materials that just weren’t possible before. This particular molecule, featuring the distinctive spiro[3.5]non-1-en-1-yl core, didn’t land here by accident. Synthetic chemists looked at gaps in current scaffolds, and through iterative design, built up the layered structure with each group serving a real function: the bromo substituent opens up cross-coupling options, while the oxo group moderates electronic properties. Such changes make all the difference once you’re trying to nudge a stubborn reaction or design a probe capable of sorting out minor changes in a biological system.
Anyone who has handled routine amino acid derivatives for linker chemistry recognizes how adding complexity to a backbone brings both challenge and opportunity. The addition of the Naphthid-1-Ylamino segment is more than decorative. Aromatic extensions may expand possible binding or stacking interactions. L-Phenylalanine itself is a building block in many peptide frameworks, but weaving it with spiro and naphthyl motifs takes the discussion out of theory and into application. I remember working with phenylalanine derivatives in a university peptide lab, and options were always limited to the same bland ring modifications. This new structure offers a fresh alternative.
Specs and detail sheets can be dull unless put into context. You don't need to see a wall of numbers to learn why this compound matters. Traditional phenylalanine derivatives, even those used in advanced research, rarely go beyond simple alkyl or halogen substitutions. Here, the spiro skeleton and fused naphthyl system shape the three-dimensional profile, which matters when navigating binding pockets or trying to control the spatial position of a functional side chain.
One important aspect lies in the bromo group at the 2-position. In modern organic chemistry, brominated aromatics often serve as “relay stations” for Suzuki, Sonogashira, or Stille couplings. Anyone working in medicinal chemistry or materials science has run into bottlenecks finding intermediates that provide enough synthetic flexibility without adding background reactivity. Most of my grad lab’s struggles came down to the lack of a reliable, versatile handle on an otherwise crowded molecule. This spiro-phenylalanine offers that rare combination.
As for the oxospiro core, it reminds me of attempts to mimic natural products with complex, rigid scaffolds. Spiro cycles introduce a bend, which often leads to unique electronic effects and improved selectivity for downstream modification, something generic flat backbones can't deliver.
Another subtlety comes from the naphthidylamine segment. Extended aromatic systems are old friends to anyone working with fluorescence probes. I’ve spent plenty of time adjusting excitation and emission in the hopes of seeing something measurable and reproducible in a biological assay. It’s not a stretch to imagine this molecule being used either directly or as part of a new dye scaffold for imaging or tracking agents.
Having an innovative molecule on hand can change the direction of research. For example, in peptide drug development, side chain modifications often mean the difference between a dead end and a promising hit. Normally, peptide chemists reach for derivatives based on ease of synthesis and commercial availability, which limits exploration. This compound pushes the boundaries by introducing more geometry and electronic diversity than you see in most off-the-shelf amino acid derivatives.
The brominated spiro core stands out to synthetic chemists aiming for diversity-oriented synthesis. Constructing molecular libraries becomes far less monotonous once you have access to a chiral, bulky, and heteroatom-rich residue. Imagine coupling this molecule into the heart of a peptide chain. The result isn’t just another repetitive fragment—it transforms how that peptide folds, interacts, and maybe even gets recognized by enzymes or receptors.
On the side of analytical science, the naphthyl group isn’t just eye-catching. Pinning down site-specific labeling has plagued many protein and nucleic acid researchers. The rigid, fused all-aromatic system can act as a fluorescent marker or an affinity tag, where previously only simple, low-specificity groups existed. The benefits echo through enzyme-substrate studies and real-time tracking experiments. From my interactions with structural biology researchers, their biggest complaint is “blunt instruments” that add noise rather than sharpen the findings. Well-crafted molecules like this bridge that gap.
Drug discovery platforms have also begun seeking more exotic scaffolds—largely because old tricks hit new walls as targets become trickier. A brominated spiro-amino acid like this brings new topology to early-stage screening. Peptides or small molecules built from it could slip into tight active sites or interact with new protein surfaces in ways flat, traditional backbones just cannot. This directly benefits screens seeking allosteric modulators or non-classical enzyme inhibitors, where structural shape often takes the lead over just simple charge or size.
Some compounds look different only on paper. With this phenylalanine derivative, functionality is baked into every piece. Let’s start with the spiro system, a dramatic shift from standard extended chains. The three-dimensional shape this feature brings can convert an inert sequence into an active motif. This is crucial for a wide range of research fields, from peptide chemistry to supramolecular design.
To put it bluntly, standard analogs in the phenylalanine family rarely offer this balance of bulk and versatility. Most commercial side-chain modifications stay in the realm of light alkylation or straightforward halogenation, putting a “paint-by-numbers” cap on creative chemical biology. By leveraging the bromo group and spiro configuration, this compound sidesteps the flatness problem and lets researchers navigate steric space with far more accuracy.
Comparing usage with older compounds, I see a clear upgrade in synthetic flexibility. The compound's chiral center—retaining the natural L-configuration—makes it easy to integrate into peptides without needing corrections for stereochemical mismatch. In my experience, working with D-amino acid analogs only adds headache downstream in biochemical or cellular work. Here, the L-form aligns with natural enzymatic recognition.
The aromatic naphthylamino extension gives new possibilities in both non-covalent stacking and optical properties. Compounds in the same family rarely sport such heavy, extended aromatic bulk; trying to replicate such features through post-synthesis alkylations proves both labor-intensive and prone to unwanted by-products. Discovering a ready-to-incorporate building block with this architecture moves research forward by weeks, if not months.
The molecule also offers improved handleability in cross-coupling chemistry. Bromide remains the halogen of choice in many palladium-catalyzed protocols, giving an edge over both chloride and iodide analogs in terms of yield and selectivity. At the same time, the structure keeps reactive groups separated by a “safe distance,” averting typical problems like competing cyclizations or decomposition seen in more fragile intermediates. Having spent days chasing up side reactions with less robust substrates, I can attest to the frustration erased by a durable, thoughtfully designed core like this one.
Curiosity leads to unexpected uses. Peptide synthesis, materials science, and biological labeling all stand to gain from what this unique molecule brings to the table. The pharmaceutical world’s shift toward non-traditional molecules underscores its value. With regulatory bodies like the FDA and EMA looking closely at molecular novelty, compounds like this carve out space in both new drug modalities and improved analytical tools.
Even in academia, where funding and time are always tight, researchers need purpose-built tools. The compound’s spiro cycle and bromo handle cut down the time and risk associated with hard-to-make building blocks. Labs no longer have to force generic amino acids into roles they were never designed to handle; having a molecule that fits the purpose brings clarity and efficiency. I’ve seen project plans trimmed from years to months simply because the right intermediate was available.
Another budding area is molecular imaging. The naphthyl system, tied to phenylalanine’s backbone, points toward both native fluorescence and extended absorption. If you’ve ever worked with protein dyes, you know the pain of quenching, poor solubility, or unclear readings. Putting a complex aromatic right into the backbone strengthens emission and absorption signatures. This could help spike the sensitivity of next-generation diagnostic platforms—an area where the field has hit a wall with “one-size-fits-all” reagents.
Experience with mainstream suppliers has taught researchers one thing: consistency counts. New molecules often tempt with promise, then disappoint with batch-to-batch variation or instability during transit. Products built for research environments need both purity and ruggedness—especially when researchers invest time and grant funding into multi-step syntheses or screening platforms.
The detailed design of N-(2-Bromo-3-Oxospiro[3.5]Non-1-En-1-Yl)-4-(2,7-Naphthid-1-Ylamino)-L-Phenylalanine pays special attention to real-world lab needs. Features like chemical purity, verified stereochemistry, and robust packaging eliminate extra rounds of troubleshooting. In the past, I’ve lost weeks to mystery by-products or racemization in similar advanced intermediates, only to discover inconsistent supply chains. High-end chemistry cannot tolerate such setbacks, and it’s clear that with this molecule, attention to detail runs from bench to bottle.
The track record for reliability grows with testimonials from top-tier institutions, across both basic and applied chemistry programs. Researchers value transparency in sourcing, rigorous analytical data, and the peace of mind that their next experiment won’t fail because of an off-spec intermediate. This trust grows with each successful synthesis, each experiment that hits the mark with clean, reproducible results.
Limits in research tend to reflect available tools, not imagination. Over time, the list of “untouchable” targets largely shrunk for one reason: chemists kept inventing more advanced building blocks. I’ve watched entire fields leap forward the moment a troublesome intermediate finally became widely available. In peptide chemistry, for instance, the addition of a sterically demanding spiro-phenylalanine like this one pushes new architectures within range. This means fresher secondary structures, tighter turns, and proteins or conjugates that don’t conform to old rules.
For synthetic organic chemists, the mixture of bromo, oxo, and spiro features opens up new retrosynthetic pathways. Instead of cobbling together fragile intermediates, you can plan bold, direct modifications. This reminds me of the moment certain cross-coupling reagents moved from specialty shops into standard catalogs: the change rippled out across the field, sparking new project proposals and patent filings.
In early-stage drug lead discovery, even a single new side chain can lead to breakthroughs. The unique shape, electronic profile, and handleability of this molecule means more “chemical space” becomes accessible. For teams focused on allosteric regulators, protein-protein interaction disruptors, or selective imaging probes, the chances of success tick upward. That means both industry and academic labs get more value from every dollar and hour spent.
The synthetic chemist’s lament rarely changes: promising starting materials don’t survive rough conditions, or they bring so much reactivity to the table that controlling downstream transformations becomes impossible. Standard phenylalanine derivatives all tend to hit similar walls, struggling with limited selectivity in cross-couplings or proving too bland for meaningful modification. Here, the structure’s inherent stability and modular functionality offer a tangible fix.
The spiro backbone blocks undesired conformational collapse, stabilizing peptides against proteolytic degradation and unlocking new cyclization routes. The bromo handle streamlines late-stage modification—making it easier to tack on larger, more complex functions without expensive protecting group strategies. In my own work, peeling away unnecessary steps can mean the difference between chasing a promising lead and shelving it due to lack of resources or time.
Cross-coupling on sensitive substrates often faces low yield and unexpected by-products. The careful placement of bromine—sufficiently reactive but not hyperactive—lets researchers fine-tune reaction partners, reducing waste and unpredictability. Besides, the compound’s architectures resist “side reactions on autopilot,” a headache for anyone optimizing conditions across a screen of analogs.
The naphthylamino group further broadens scope by increasing compatibility with both organic solvents and biological contexts. Many high-performance amino acid derivatives fall short because they lack adequate solubility or display toxic by-products. By matching polar and nonpolar regions within this molecule, designers have built in improved balance for both synthesis and downstream bio-assays—a detail that’s frequently overlooked but vital for real-world application.
Building trust calls for facts, not just promise. Principal studies in medicinal and synthetic chemistry show a steady trend toward complex, chiral intermediates with multiple orthogonal functionalities. Peer-reviewed articles and patent filings focus more and more on building blocks that decrease synthetic steps and reduce failures by treating new molecule design as a true multidisciplinary problem.
Research published in journals like Journal of the American Chemical Society and Angewandte Chemie highlights the benefits of spiro-fused amino acid derivatives across enzyme inhibition, probe design, and advanced material creation. Reformulating peptide backbones with bulkier, more complex residues leads not only to differences in secondary structure but also to measurable improvements in biological half-life and target retention—key goals in drug and diagnostics research.
On the practical side, safety protocols for advanced electrophilic, aromatic, and heterocyclic reagents rely on well-established guidelines. The synthetic pathway and anticipated reactivity of N-(2-Bromo-3-Oxospiro[3.5]Non-1-En-1-Yl)-4-(2,7-Naphthid-1-Ylamino)-L-Phenylalanine falls inside those boundaries. Researchers familiar with halogenated aromatics and spirocyclic scaffolds recognize both the challenges and real steps needed to mitigate risks, from small-scale weighing to careful waste management.
Ethical and environmental standards in chemistry continue climbing. Sourcing specialty building blocks directly from high-reputation suppliers ensures traceability. Modern production methods cut down waste, support batch consistency, and align with increasingly strict global standards for both workplace safety and environmental footprint. Through years of working in commercial and academic labs, I’ve seen more projects succeed when supply chains and manufacturing protocols match the demands of sensitive, bioriented synthetic chemistry.
Growth in chemical research unfolds along two axes: technical possibility and responsible progress. Sophisticated molecules like this one force a conversation about smarter, more sustainable manufacturing. Structured building blocks speed up discovery science but also hold the potential for targeted, minimal-waste processes. Where older analogs forced researchers to burn through solvents and time, today’s specialty compounds increase “bang for the buck,” cutting down environmental impact.
Ongoing efforts in green chemistry point to modular, robust building blocks as key to reducing overall emissions and chemical waste. Spirocyclic, high-functionality amino acid derivatives align with this vision. Researchers developing next-generation peptide therapeutics or smart biomaterials benefit from tools designed for efficiency and selectivity rather than brute-force compatibility.
Those hesitating over “new” compounds may recall earlier experiences with unproven or unreliable intermediates. But as more labs switch to advanced building blocks and report their results, confidence builds. Scientific forums and community-driven databases help validate claims, keep suppliers accountable, and point out both good and bad actors along the supply chain.
Innovation in chemistry rarely announces itself with fanfare. New molecules like N-(2-Bromo-3-Oxospiro[3.5]Non-1-En-1-Yl)-4-(2,7-Naphthid-1-Ylamino)-L-Phenylalanine drive research forward because they embody thoughtful, needs-driven design rooted in a deep understanding of real-world laboratory obstacles and solutions. With every feature serving real, substantiated purposes—whether in synthetic access, biological compatibility, or advanced analytical work—this compound exemplifies the gains waiting just beyond the comfort zone of routine reagents.
Scientists worldwide continue to innovate and solve urgent problems, provided they have the right tools. This molecule signals a new set of possibilities—not because it breaks the rules, but because it builds on hard-won insights from practical lab experience, published research, and growing consensus about what works. In this fast-evolving landscape, well-made, multi-functional molecules will keep turning today’s questions into tomorrow’s solutions.