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What is the chemical structure of Dess-martin (1,1,1 - triacetoxy - 1,1 - dihydro - 1,2 - benziodoxol - 3 (1h) -one)?
The chemical structure of Dess-Martin (1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxacyclopentene-3 (1H) -one) is a key part of organic synthesis chemistry. Its structure contains a benzo five-membered heterocyclic ring in which the iodine atom is adjacent to the oxygen atom. The unique heterocyclic structure endows the compound with specific chemical activity.
The benzene ring part of the heterocyclic ring of this compound has an aromatic and stable structure, providing a certain stability for the whole molecule. The three acetoxy groups connected to the iodine atom add many changes to its chemical properties. The presence of acetoxy groups not only affects the spatial configuration of molecules, but also plays an important role in chemical reactions. They can participate in a variety of organic synthesis steps through reactions such as nucleophilic substitution.
Dess-Martin reagents are often used in the oxidation reaction of alcohols in the field of organic synthesis, and can efficiently convert alcohols into corresponding alcaldes or ketones. The iodine atom in its structure is in a high oxidation state, which is a key factor in realizing the oxidation reaction. The unique chemical structure makes Dess-Martin reagents exhibit good selectivity and reactivity in the process of organic synthesis, providing a powerful tool for organic synthesis chemists to help build various complex organic molecular structures.
What are the common applications of Dess-martin (1,1,1 - triacetoxy - 1,1 - dihydro - 1,2 - benziodoxol - 3 (1h) -one) in organic synthesis?
Dess-Martin (1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxacyclopentene-3 (1H) -one) is widely used in organic synthesis.
First, it is often used in the oxidation of alcohols. Primary alcohols can be efficiently and selectively oxidized to formaldehyde, and secondary alcohols can be oxidized to ketones. Compared with traditional oxidation methods, its advantages are significant. For example, although traditional chromium reagents can achieve similar transformations, chromium reagents are toxic and unfriendly to the environment. The Dess-Martin reagent has mild reaction conditions, simple operation, and few side reactions, and the product is easy to separate and purify. Taking benzyl alcohol oxidation as an example, using Dess-Martin reagent, benzyl alcohol can be smoothly converted into benzaldehyde in dichloromethane solvent for a few hours at room temperature, and the yield is quite high.
Second, it is also often seen in the field of total synthesis of complex natural products. Due to its selective oxidation characteristics, it can precisely realize the oxidation of alcohol hydroxyl groups at specific positions and help to construct complex molecular structures. In the synthesis of steroid natural products, specific alcohol hydroxyl groups can be oxidized to corresponding carbonyl groups according to molecular design requirements, laying the foundation for the subsequent construction of steroid parent nuclei and the introduction of other functional groups.
Third, it also has important applications in the field of medicinal chemistry. In the process of new drug development, the molecular structure of the drug is often modified to anoxidize alcohols into alcaldes or ketones. Dess-Martin reagent can meet such needs, ensure the efficient and high selectivity of the reaction, and help obtain the target drug molecule. For example, in the synthesis of a new anti-tumor drug intermediate, this reagent is used to oxidize the alcohol hydroxyl group to successfully achieve key structural transformation.
What safety precautions should be paid when using Dess-martin (1,1,1 - triacetoxy - 1,1 - dihydro - 1,2 - benziodoxol - 3 (1h) -one)?
When using Dess-Martin (1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxacyclopentene-3 (1H) -one), the following safety precautions should be paid attention to.
This reagent is highly oxidizing and should be stored away from flammable and reducing substances, such as alcohols, mercaptan, etc., because contact with it can easily cause violent reactions, even fire and explosion. The use process must be operated in a well-ventilated environment, such as a fume hood, because the gas produced by the reaction may be harmful, and good ventilation can be dispersed in time to ensure the safety of the experimenter.
Wear protective clothing, gloves and goggles when operating. Protective clothing can prevent the reagent from contacting the body, gloves prevent the skin of the hand from contacting it, and goggles protect the eyes from the damage of the reagent splashing. The action of weighing and transferring the reagent should be gentle and precise to avoid the spill of the reagent. If it is accidentally spilled, it should be handled immediately according to relevant regulations to prevent dangerous reactions with other substances.
In addition, the reaction device using the reagent should ensure that it is well sealed to prevent the reagent from accidentally reacting with external substances. At the same time, it is necessary to be familiar with its emergency treatment methods. If it accidentally touches the skin or eyes, it should be rinsed with plenty of water immediately and seek medical attention in time. In short, when using Dess-Martin reagent, safety procedures must be strictly followed to ensure the safety of the experiment
What are the methods for preparing Dess-martin (1,1,1 - triacetoxy - 1,1 - dihydro - 1,2 - benziodoxol - 3 (1h) -one)?
The preparation method of Dess-Martin (1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxacyclopentene-3 (1H) -one) is quite delicate. Common preparation methods are as follows:
The starting material is selected from o-iodobenzoic acid, which is co-heated with acetic anhydride, and through the step of dehydration and cyclization, 1-hydroxy-1,2-benzoiodoxacyclopentene-3 (1H) -one can be generated. This process is like smelting stones by fire, so that the raw material coagulates and changes at high temperature.
Then, the obtained product is mixed with acetic anhydride and acetic acid, an appropriate amount of sodium acetate is added, and the reaction is heated up. This step is like a carefully prepared formula, the phases are combined, and the transformation is slow. Under the control of suitable temperature and time, the hydroxyl group is gradually replaced by the acetoxy group, and then the Dess-Martin reagent is obtained.
With o-iodobenzoic acid as the base, it first reacts with oxalyl chloride to form o-iodobenzoyl chloride. After a series of reactions, such as interacting with specific reagents, the target product can finally be obtained. This path seems to be a winding road, although the steps are different, it can achieve the purpose of preparation. When preparing, it is necessary to pay attention to many factors such as reaction temperature, time, and proportion of raw materials. If there is a slight difference, it will be difficult to obtain pure products.
What are the advantages of Dess-martin (1,1,1 - triacetoxy - 1,1 - dihydro - 1,2 - benziodoxol - 3 (1h) -one) over other similar reagents?
The Dess-Martin reagent, that is, 1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxacyclopentene-3 (1H) -one, is indeed more extraordinary than other similar reagents.
The first advantage is that the reaction conditions are mild. Ordinary oxidation methods may require high temperature hot topics, or rely on strong bases and strong acids, and many sensitive groups are easily damaged under these conditions. However, the Dess-Martin reagent can exert its oxidation ability only at room temperature or slightly warmed conditions, and among many complex organic molecules, fragile functional groups can also be unharmed. For example, if a compound containing an enol ether structure is treated with a strong oxidizing reagent, the enol ether is easily hydrolyzed or rearranged, and then oxidized with Dess-Martin reagent. The enol ether structure is as stable as Mount Tai, and the oxidation reaction smoothly reaches the expected target.
Furthermore, its selectivity is very good. In many systems where oxidizable check points coexist, it can accurately act on specific groups. For example, in polyols, when primary and secondary alcohols coexist, Dess-Martin reagents often preferentially oxidize primary alcohols to alaldehyde, with little interference to secondary alcohols, just like archers take the head of a general in the middle of the army without disorder.
And the reaction rate is quite fast and the efficiency is quite high. Compared with some oxidizing reagents that require a long reaction cycle, Dess-Martin reagents can often complete the reaction within a few hours, greatly shortening the reaction time and improving the output efficiency. This is of great significance in large-scale preparation and time-critical experiments, just like marching to war, quick and quick, saving a lot of resources and energy.
And because of its relatively simple post-processing. After the reaction is completed, only simple extraction, washing and other conventional operations can effectively separate the product and reagent residues, without cumbersome and complicated separation processes, like a light boat in a canal, free of obstacles, saving a lot of trouble for the follow-up work of organic synthesis.