|
1,3-Dithiolane
1,3-Dithiolane is the organosulfur compound with the formula . Also classified as a heterocycle related cyclopentane by replacing two methylene bridges ( units) with thioether groups. It is an isomer of 1,2-dithiolane. 1,3-Dithiolanes are compounds where one or more H atoms of the parent 1,3-dithiolane are replaced by other groups. These species are more widely studied. Synthesis A common family of 1,3-dithiolanes have the formula . They are obtained by treating an aldehyde with 1,2-ethanedithiol. Related compounds with the formula are obtained by condensation of 1,2-ethanedithiol with ketones. The dithiolane protected aldehydes and ketones are amenable to many reactions without perturbing the dithiolane ring. Dithiolanes can often be reverted, i.e., deprotected, to the parent aldehyde and ketone. A variety of reagents have been developed for that purpose. Reactions 1,3-Dithiolanes derived from aldehydes can be deprotonated: : These organolithium compounds degrade with ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,2-dithiolane
1,2-Dithiolane is an organosulfur compound with the formula . It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges ( units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally. The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization. In general, 1,3-dithiols are superior reductants relative to monothiols. Natural occurrence Many substituted 1,2-dithiolates are found in nature. The most common is lipoic acid, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for aerobic metabolism in mammals. Some 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus. The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethane-1,2-dithiol
Ethane-1,2-dithiol, also known as EDT, is a colorless liquid with the formula C H( SH). It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions. Preparation Ethane-1,2-dithiol is made commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis. Reactions 1,2-Ethanedithiol is a weak acid, typical of alkyl thiols. In the presence of base and an alkylating agent, 1,2-ethanedithiol converts to thioethers: : Oxidation of 1,2-ethanedithiol gives a series of oligomers, including the cyclic bis(disulfide). As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates. Other 1,2- and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organosulfur
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and carbon–te ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of py ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclopentane
Cyclopentane (also called C pentane) is a highly flammable alicyclic compound, alicyclic hydrocarbon with chemical formula C5H10, C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It is a colorless liquid with a petrol-like odor. Its freezing point is −94 °C and its boiling point is 49 °C. Cyclopentane is in the class of cycloalkanes, being alkanes that have one or more carbon rings. It is formed by cracking (chemistry), cracking cyclohexane in the presence of alumina at a high temperature and pressure. It was first prepared in 1893 by the German chemist Johannes Wislicenus. Production, occurrence and use Cycloalkanes are formed by catalytic reforming. For example, when passed over a hot platinum surface, 2-Methylbutane, 2-methylbutane converts into cyclopentane. Cyclopentane is principally used as a blowing agent in the manufacture of polyurethane foam, polyurethane insulating foam, replaci ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylene Bridge
In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, as in "methylene chloride" (dichloromethane ). As a bridge in other compounds, for example in cyclic compounds, it is given the name methano. However, the term methylidene group (not to be confused with the term methylene group, nor the carbene Methylene (compound), methylidene) properly applies to the group when it is connected to the rest of the molecule by a double bond (), giving it chemical properties very distinct from those of a bridging group. Organic chemistry It is the repeating unit in the skeleton of the unbranched alkanes. Polyethylene also can be called polymethylene. Compounds possessing a methylene bridge located between two electron withdrawing groups (such as Nitro compound, nitro, carbonyl or nitrile groups) are som ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioether
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, Volatile organic compound, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. Nomenclature Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Structure and bonding Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The bond length is about 120–122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are solubl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,2-ethanedithiol
Ethane-1,2-dithiol, also known as EDT, is a colorless liquid with the formula C H( SH). It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions. Preparation Ethane-1,2-dithiol is made commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis. Reactions 1,2-Ethanedithiol is a weak acid, typical of alkyl thiols. In the presence of base and an alkylating agent, 1,2-ethanedithiol converts to thioethers: : Oxidation of 1,2-ethanedithiol gives a series of oligomers, including the cyclic bis(disulfide). As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates. Other 1,2- and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula . Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, ''e.g.'', testosterone, and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introdu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Protecting Group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, specific parts of the molecules cannot survive the required reagents or chemical environments. These parts (functional groups) must be protected. For example, lithium aluminium hydride is a highly reactive reagent that usefully reduces esters to alcohols. It always reacts with carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must be prevented. One way to do so converts the carbonyl into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the hydride step is complete, aqueous acid removes the acetal, restoring the carbonyl. This step ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
