isoquinoline 2-oxide

The chemical structure of isoquinoline + 2-oxide is unique. Isoquinoline is an aromatic compound containing nitrogen heterocycles, which is similar to the structure of quinoline, but the position of the nitrogen atom is different.
In the structure of isoquinoline-2-oxide, the parent nuclear skeleton of isoquinoline is unchanged, and it is formed by fusing a phenyl ring with a nitrogen-containing pyridine ring. This fused structure endows isoquinoline with many special chemical properties. Due to the existence of its conjugate system, it has certain stability and aromaticity.
And "-2-oxide" is called, the nitrogen atom at position 2 on the guiyin isoquinoline ring oxidizes to form a nitrogen-oxygen double bond (N → O). The introduction of this nitrogen-oxygen double bond significantly changes the electron cloud distribution of the molecule. After the nitrogen atom forms a lone pair of electrons, the electron cloud is biased towards the oxygen atom, which reduces the electron cloud density around the nitrogen atom, thereby affecting the polarity and chemical reactivity of the whole molecule.
From the perspective of spatial structure, the existence of nitrogen-oxygen double bonds or changes in the molecular spatial conformation have an impact on their interactions with other molecules, such as hydrogen bond formation 、π - π stacking. These structural changes make isoquinoline-2-oxide show unique application value in organic synthesis, pharmaceutical chemistry and other fields. It can provide unique structural units for the construction of novel compounds, or based on its special structure to develop drug molecules with specific biological activities.

The common physical properties of isoquinoline-2-oxide are as follows:
It is mostly in solid form at room temperature and pressure. This is due to the interaction between molecules such as van der Waals forces and hydrogen bonds, which makes the molecular arrangement relatively regular and tight, so that it can be shown as a solid state.
Isoquinoline-2-oxide has a certain melting point. The melting point value depends on its own structure and the strength of the intermolecular forces. Because the molecule contains oxygen atoms, hydrogen bonds can be formed, which enhances the intermolecular forces, resulting in a relatively high melting point. However, the specific melting point will vary due to factors such as purity.
In terms of solubility, isoquinoline-2-oxide exhibits different solubility in organic solvents. It often has good solubility in polar organic solvents, such as ethanol and acetone. This is because its molecular structure has a certain polarity, and it can be dissolved with polar organic solvents through the interaction of intermolecular forces through the principle of similar miscibility. However, in non-polar organic solvents, such as n-hexane, the solubility is poor. Due to the weak intermolecular force between non-polar solvents and isoquinoline-2-oxide, it is difficult to overcome the original intermolecular force to disperse and dissolve it.
From the appearance point of view, pure isoquinoline-2-oxide usually appears white to light yellow solid powder. Its color is related to purity, and if it contains impurities, the color may be deepened. And the substance has a certain smell, but the smell is not strong and pungent, relatively mild.
The density of isoquinoline-2-oxide is also an important physical property. Its density is related to the molecular weight and the way of molecular packing. Due to the compact molecular structure, the density is higher than that of some light organic compounds. However, the exact density value needs to be accurately determined by experiments.

Isoquinoline-2-oxide is useful in many fields. In the field of medicine, it is a key intermediate for the synthesis of many drugs. For example, in the research and development of antimalarial drugs, this compound has a unique chemical structure, which can combine with specific targets in the malaria parasite, interfere with its metabolic process, and achieve anti-malarial effect. In the creation of anti-tumor drugs, its structure can be modified to enhance the targeting of tumor cells and inhibit the proliferation of tumor cells.
In the field of materials science, isoquinoline-2-oxide is also useful. It can be used as a raw material for the synthesis of organic semiconductor materials. Because its structure contains nitrogen and oxygen heteroatoms, it imparts specific electrical and optical properties to the material. The organic thin film transistor prepared by this method exhibits good carrier mobility and has great application potential in the field of flexible electronic devices. And in terms of luminescent materials, through rational molecular design, it can emit light of specific wavelengths, which is applied to the manufacture of organic Light Emitting Diodes (OLEDs) to improve the display effect.
In the field of chemical synthesis, isoquinoline-2-oxide is an important synthesis block. It can participate in a variety of organic reactions, such as nucleophilic substitution, redox, etc. With its chemical activity, complex organic molecular structures can be constructed, providing an effective path for the synthesis of fine chemicals, fragrances, etc. For example, the preparation of some unique fragrances, through specific reactions, introduce them into the molecular structure of fragrances, giving fragrances a unique and lasting aroma.
Isoquinoline-2 -oxide plays an important role in many fields such as medicine, materials science and chemical synthesis, and has made great contributions to promoting the development of various fields.

The method of making isoquinoline-2-oxide, as mentioned in ancient books, probably has several ways.
First, it can be obtained by oxidation of isoquinoline. Peroxides are often used as oxidants, such as m-chloroperoxybenzoic acid (m-CPBA), which interacts with isoquinoline. Under suitable reaction conditions, the nitrogen atom of isoquinoline can be oxidized, and then isoquinoline-2-oxide can be formed. This reaction is mild, the yield is quite good, and the operation is relatively simple. It is a commonly used method.
Second, there is also a method of using metal catalysts to assist oxidation. For example, in an appropriate oxidation system, transition metal salts such as tungstate and molybdate are used to coordinate oxidants, such as hydrogen peroxide, to promote the oxidation reaction of isoquinoline, which can be directed to the target product. This approach uses the characteristics of metal catalysts to regulate the reaction process, which can improve the selectivity and efficiency of the reaction.
Third, in organic synthesis, oxygen atoms can also be introduced by constructing an isoquinoline ring to prepare isoquinoline-2-oxide. With suitable nitrogen and carbon-containing raw materials, the isoquinoline parent nucleus is constructed through multi-step reactions, and oxygen atoms are ingeniously introduced in specific steps. This strategy requires precise design of the reaction route and fine control of the reaction conditions.
All methods have their own advantages and disadvantages. In practical application, the appropriate method should be carefully selected according to factors such as the availability of raw materials, reaction cost, and purity requirements of the target product, in order to achieve the best synthetic effect.

The stability of isoquinoline-2-oxide depends on its chemical structure, electronic effect and environment. This compound has a heterocyclic aromatic hydrocarbon structure, and the nitrogen atom is connected to the oxygen atom to form an N-O bond.
From the structural point of view, the isoquinoline ring is a conjugated system, which is aromatic and endows the molecule with certain stability. However, in the N-O bond, the electronegativity of oxygen is higher than that of nitrogen, causing the electron cloud to be biased towards oxygen, making nitrogen partially positively charged. This charge distribution may affect the stability of the molecule, because the positively charged nitrogen is vulnerable to attack by nucleophiles.
The electronic effect is also critical. The substituents on the isoquinoline ring can affect the stability of N-O bonds by inducing and conjugating effects. Electron-withdrawing groups can disperse the positive charge of nitrogen atoms and enhance stability; electron-withdrawing groups intensify the accumulation of positive charges and weaken stability.
Environmental factors have a significant impact on its stability. With the increase of temperature, the thermal motion of molecules intensifies, the vibration of N-O bonds is enhanced, or the bond is broken, resulting in a decrease in stability. In acid-base environment, the protonation or deprotonation reaction or changes the molecular charge distribution and structure, which affects the stability. In acidic media, nitrogen atom or protonation makes the electron cloud of N-O bond more inclined to oxygen and weakens the bond; in alkaline media, deprotonation reaction or structural change affects stability.
Solvents also play a role. Different solvents interact differently with isoquinoline-2-oxide, and polar solvents or interact with polar N-O bonds to affect its stability.
Overall, the stability of isoquinoline-2-oxide is influenced by a variety of factors, which jointly determine its stability under specific conditions.