|
Macrocycles
Macrocycles are often described as molecules and ions containing a Ring (chemistry), ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry. Synthesis The formation of macrocycles by ring-closure is called macrocyclization. The central challenge to macrocyclization is that ring-closing reactions do not favor the formation of large rings. Instead, medium sized rings or polymers tend to form. Early macrocyclizations were achieved ketonic decarboxylations for the preparation of terpenoid macrocycles. So, while Ružička was able to produce various macrocycles, the yields were low. This kinetic problem can be addressed by using high-dilution reactions, whereby intramolecular processes are favored relative to polymerizations. Reactions amenable to high dilution include Dieckmann condensation and related based-induced reactions of esters with remote halides. So ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ring-closing Metathesis
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various Saturated and unsaturated compounds, unsaturated rings via the intramolecular olefin metathesis, metathesis of two terminal alkenes, which forms the cycloalkene as the ''E-'' or ''Z-'' isomers and Volatility (chemistry), volatile ethylene.Carey, F. A.; Sunburg, R. J. Reactions Involving Transition Metals. ''Advanced Organic Chemistry: Reaction and Synthesis'', 5th Ed.; Part B; Springer: New York, 2010, pp. 761-767.Monfette, S.; Fogg, D. E. (2009). "Equilibrium Ring-Closing Metathesis". ''Chem. Rev.'' 109 (8): 3783-3816. . The most commonly synthesized ring sizes are between 5-7 atoms;Deiters, A.; Martin, S. F. (2004). “Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis”. ''Chem. Rev.'' 104 (5): 2199-2238. . however, reported syntheses include 45- up to 90- membered macroheterocycles.Cain, M. F.; Forrest, W. P.; Pery ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclodextrin
Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocycle, macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds. Cyclodextrins are produced from starch by enzyme, enzymatic conversion. They are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering. Cyclodextrins are composed of 5 or more α-D-glucoPyranose, pyranoside units linked 1 → 4, as in amylose (a fragment of starch). Typical cyclodextrins contain a number of glucose monomers ranging from six to eight units in a ring, creating a cone shape: * α-Cyclodextrin, α (alpha)-cyclodextrin: 6 glucose subunits * β-Cyclodextrin, β (beta)-cyclodextrin: 7 glucose subunits * γ-Cyclodextrin, γ (gamma)-cyclodextrin: 8 glucose subunits The largest well-characterized cyclodextrin contains 32 1,4-anhydroglucopyranoside units. Poorly-characterized mixtures, containing at least 150-membered cyclic oligosaccharides are also ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Calixarene
A calixarene is a macrocycle or cyclic oligomer based on a methylene-linked phenols. With hydrophobic cavities that can hold smaller molecules or ions, calixarenes belong to the class of cavitands known in host–guest chemistry. Nomenclature Calixarene nomenclature is straightforward and involves counting the number of repeating units in the ring and including it in the name. A calix rene has 4 units in the ring and a calix rene has 6. A substituent in the meso position Rb is added to the name with a prefix C- as in C-methylcalix rene The word calixarene is derived from the Greek calix or chalice because this type of molecule resembles a vase (or cup) and from the word arene that refers to the aromatic building block. Synthesis Calixarenes are generally produced by condensation of two components: an electron-rich aromatic compound, classically a 4-substituted phenol, and an aldehyde, classically formaldehyde. *The scope for the aromatic component is broad diverse. The ke ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Muscone
Muscone is a macrocycle, macrocyclic ketone, an organic compound that is the primary contributor to the odor of deer musk. Natural muscone is obtained from musk, a glandular secretion of the musk deer, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery and for scenting consumer products today is synthetic. It has the characteristic smell of being "musky". Chemical structure and synthesis The chemical structure of muscone was first elucidated by Leopold Ružička. It is a 15-membered ring ketone with one methyl substituent in the 3-position. It is an oily liquid that is found naturally as the (−)-enantiomer, (''R'')-3-methylcyclopentadecanone. Muscone has been synthesized as the pure (−)-enantiomer as well as the racemate. It is very slightly soluble in water and miscible with alcohol. One asymmetric synthesis of (−)-muscone begins with commercially av ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Erythromycin A
Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used during pregnancy to prevent Group B streptococcal infection in the newborn, and to improve delayed stomach emptying. It can be given intravenously and by mouth. An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn. Common side effects include abdominal cramps, vomiting, and diarrhea. More serious side effects may include ''Clostridioides difficile'' colitis, liver problems, prolonged QT, and allergic reactions. It is generally safe in those who are allergic to penicillin. Erythromycin also appears to be safe to use during pregnancy. While generally regarded as safe during breastfeeding, its use by the mother during the first two weeks of life may increase the risk of pyloric stenosis in the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereogenic
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups creates a new stereoisomer. Stereocenters are also referred to as stereogenic centers. A stereocenter is geometrically defined as a point (location) in a molecule; a stereocenter is usually but not always a specific atom, often carbon. Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds. The number of hypothetical stereoisomers can be predicted by using 2''n'', with ''n'' being the number of tetrahedral stereocenters; however, exceptions such as meso compounds can reduce the prediction to below the expected 2''n''. Chirality centers are a type of stereocenter with four different substituent groups; chirality centers are a specific subset of stereocenters because they can only ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereoselectivity
In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non- stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite: both products are at least possible and merely differ in amount. However, in favorable cases, the minor stereoisomer may not be detectable by the analytic methods used. An enantioselective reaction is one in which one enantiomer is formed in preference to the other, in a reaction that creates an optically active product from an achiral starting material, using either a chiral catalyst, an enzyme or a chiral reagent. The degree of selectivity is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are Precursor (chemistry), precursors to nylon. Cyclohexyl () is the alkyl substituent of cyclohexane and is abbreviated Cy. Production Cyclohexane is one of components of naphtha, from which it can be extracted by advanced distillation methods. Distillation is usually combined with isomerization of methylcyclopentane, a similar component extracted from naphtha by similar methods. Together, these processes cover only a minority (15-20%) of the modern industrial demand, and are complemented by synthesis. Modern industrial synthesis On an industrial scale, cyclohexane is produced by hydrogenation of benzene in the presence of a Raney nickel catalyst. Prod ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes Physical property, physical and Chemical property, chemical properties, and evaluation of Reactivity (chemistry), chemical reactivity to understand their behavior. The study of organic reactions includes the organic synthesis, chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. The range of chemicals studied chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Regiochemistry
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong Base (chemistry), base will Hydrogen atom abstraction, abstract from an Organic compound, organic molecule, or where on a substituted benzene ring a further substituent will be added. A specific example is a halohydrin formation reaction with 2-propenylbenzene: : Because of the preference for the formation of one Product (chemistry), product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other. Various examples of regioselectivity have been formulated as rules for certain classes of Chemical compound, compounds under certain conditions, many of which are named. Among the first introduced to chemistry students are Markovnikov's rule ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereochemical
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined as having the same molecular formula and sequence of bonded atoms (constitution) but differing in the geometric positioning of the atoms in space. For this reason, it is also known as 3D chemistry—the prefix "stereo-" means "three-dimensionality". Stereochemistry applies to all kinds of compounds and ions, organic and inorganic species alike. Stereochemistry affects biological, physical, and supramolecular chemistry. Stereochemistry reactivity of the molecules in question ( dynamic stereochemistry). History In 1815, Jean-Baptiste Biot's observation of optical activity marked the beginning of organic stereochemistry history. He observed that organic molecules were able to rotate the plane of polarized light in a solution or in t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Intramolecular Reaction
In chemistry, intramolecular describes a Chemical process, process or characteristic limited within the Chemical structure, structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Relative rates In intramolecular organic reactions, two reaction sites are contained within a single molecule. This configuration elevates the effective concentration of the reacting partners resulting in high reaction rates. Many intramolecular reactions are observed where the intermolecular version does not take place. Intramolecular reactions, especially ones leading to the formation of 5- and 6-membered rings, are rapid compared to an analogous intermolecular process. This is largely a consequence of the reduced entropic cost for reaching the transition state of ring formation and the absence of significant strain associated with formation of rings of these sizes. For the formation of different ring sizes via cyclization of substrates of varying tether ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
