Hydroxylation saturated carbon atoms

Alcohols are compounds whose molecules have a hydroxyl group attached to a saturated carbon atom. 

From a theoretical point of view this is an extremely interesting reaction. The displacement of a hydroxyl group from a saturated carbon atom appears to be unknown in basic solution. The fact that amino-methane sulfonic acid can be isolated from the bisulfite addition product of formaldehyde on treatment with ammonia does not prove, of course, that a direct displacement, such as is indicated in XVI to XVII, actually occurred. Furthermore, it is quite clear that preliminary formation of an imine (XVIII) is not necessary for the reaction of aromatic amines with sodium bisulfite (steps XIX to XVIII to XVII, etc.). 1-Dimethyl-aminonaphthalene-4-sulfonic acid (XX) and l-aminonaphthalene-4-sulfonic acid (XIX) show similar reaction kinetics 16a when treated with sodium bisulfite, yet with the tertiary amine (XX) it is not possible to write an imino structure corresponding to XVIII. 

One of the earliest in silico models of human bioavailability was reported by Hirono and coworkers [26]. This study employed a set of 188 compounds that were classified as low (<50%), medium (50-89%), or well (>90%) absorbed and used a classification routine, fuzzy adaptive least squares, to generate discriminant functions. The molecules were described by their physicochemical properties and substructural descriptors, which meant that functional groups or substructures that enhanced bioavailability (e.g., saturated carbon atoms in side chains) or reduced it (e.g., aliphatic hydroxyl groups) could be identified. The performance varied between the three classes with the lowest success for the well-absorbed compounds, perhaps the most important group of the three. 

Alcohols are compounds whose molecules have a hydroxyl group (— OH) attached to a saturated carbon atom. Alcohols can be described as alkyl derivatives of water where one hydrogen in the water molecule has been replaced by an alkyl (R —) group. The general formula of alcohols is R —OH and the general molecular formula of alcohols is CnH2n+1OH or CnH2n+20. 

Bloom and Shull deduced the generalization that microorganisms which can cause axial hydroxylation at a given carbon atom can also cause epoxidation of a double bond attached to the same carbon atom (B-66). The epoxide oxygen will have the same configuration as the hydroxyl group which is normally introduced at the saturated carbon atom. Their explanation of this thesis was that the pi electrons of the double... 

Alcohols have a hydroxyl (— OH) group bonded to a saturated carbon atom. The alcohol carbon atom may be part of a simple alkyl group, as in some of the following examples, or it may be part of a more complex molecule, such as cholesterol. Alcohols are also classified as 1°, 2°, or 3°, depending on the number of carbons bonded to the alcohol carbon. 

Alcohols are organic compounds whose molecules contain a hydroxyl (— OH) group covalently bonded to a saturated carbon atom. Thus if we substitute an —OH for an H in CH4, we get CH3OH, methyl alcohol. The functional group of the alcohols is — OH. The general formula for alcohols is ROH, where R is an allyl or a substituted alkyl group. 

Compounds that contain a hydroxyl group bonded to a saturated carbon atom Classification ... 

An oft encountered reaction in secondary metabolite biosynthesis is hydroxylation at saturated carbon atoms. These reactions are mediated by a mixed-function oxidase (or mono-oxygenase) i.e. an oxidase which uses molecular oxygen for hydroxylation, according to the... 

Alcohols are compounds of the general formula R-OH in which the hydroxyl group -OH is bonded to a saturated carbon atom. Three classes of alcohols can be distinguished ... 

So far, in all PHAs, which have been characterized the hydroxyl replaced carbon atom is of R configuration, except in certain special circumstances where there is no chirality. At the identical C-3 or p position an alkyl group that can differ from methyl to tridecyl, is placed. Nevertheless, this alkyl side chain is not essentially saturated unsaturated, aromatic, epoxidized, halogenated and branched monomers have been reported too (Lageveen et al., 1988 Abe et al., 1990 Doi and Abe, 1990 Fritzsche etal., 1990a,b,c Kimetal., 1991,1992 Choi and Yoon, 1994 Hazeretal.,... 

Compounds with amino or hydroxyl groups decrease in biodegradabihty relative to degree of saturation, in the following order primary, secondary, then tertiary carbon atom of attachment. 

This dry ozonation procedure is a general method for hydrox-ylation of tertiary carbon atoms in saturated compounds (Table 1). The substitution reaction occurs with predominant retention of configuration. Thus cis-decalin gives the cis-l-decalol, whereas cis- and frans-l,4-dimethylcyclohexane afford cis- and trans-1,4-dimethylcyclohexanol, respectively. The amount of epimeric alcohol formed in these ozonation reactions is usually less than 1%. The tertiary alcohols may be further oxidized to diols by repeating the ozonation however, the yields in these reactions are poorer. For instance, 1-adamantanol is oxidized to 1,3-adamantane-diol in 43% yield. Secondary alcohols are converted to the corresponding ketone. This method has been employed for the hydroxylation of tertiary positions in saturated acetates and bromides. 

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