Homologues and Analogues

Trichloromethanesulfenyl chloride has also been used for the preparation of lubricant additives (see Lubrication and lubricants). Some higher homologues and analogues of trichloromethanesulfenyl chloride have been reported, ie, trichlorovinylsulfenyl chloride [19411-15-5] 1,1,2,2-tetrachloroethanesulfenyl chloride [1185-09-7] 1,2,2,2-tetrachloroethanesulfenyl chloride [920-62-7] and pentachloroethanesulfenyl chloride [5940-94-3] (70—74). A commercial fungicide, Captafol [2425-06-17, is the reaction product of 1,1,2,2-tetrachloroethanesulfenyl chloride with tetrahydrophthalimide (75). 

Some homologues and analogues of triazaphosphaadamantane (68)—(70) have been described [Eq. (35)] (74MI3 75MI1 81VSP374584 82PS105). 

EXTENSIONS AND COMMENTARY With success in the preparation of the rather stable nor-LSD intermediate, any number of 6-substituted nor-LSD homologues and analogues can be synthesized. Simply use the appropriate alkyl bromide or alkyl iodide and the desired product will be in hand, after a modest amount of rather sophisticated purification at a micro scale. Several analogues are in the chemical literature, and some of them have been explored in direct comparison to LSD. Here are a few examples ... 

The alkaloid piperine generally is accepted as the active bite component in black pepper. The homologues and analogues of piperine are minor or trace compounds and their contribution to pungency is small. Despite the controversy over the nature of pungent compounds in pepper, piperine content has been taken as a measure of the total pungency. 

In the presence of benzene, toluene, pyridine and tiophene, considerable proportions of biphenyl and terphenyl and their homologues and analogues were formed. 

Tetryl manufacture Nitration of dimethytaniline The production of dimethylanilinc sulphate Nitration Washing the tctr> l Crystallization from benzene Crystallization from acetone Nitration of dinitromethylaniline Homologues and analogues of tetryl... 

Cinnamic add, its homologues and analogues, behave on the one hand like adds, since they form salts, esters, chlorides, amides, etc. Further, they show the properties of the ethylene series in that they take up by addition the most various kinds of atoms and groups. By the action of nascent hydrogen two atoms of hydrogen are added to the molecule of cinnamic add with a change from double to single union ... 

The 1,2-dipolar cycloaddition of chlorosulfonyl isocyanate to different cycloalkenes has become a well-known route for the synthesis of cycloalkane-fused p-lactams, and for alicyclic P-amino acids, after hydrochloric acid treatment. The addition takes places regio- and stereospecifically, in accordance with the Markovnikov orientation rule [51-55]. In this manner, a number of homologue and analogue alicyclic P amino acids have been prepared, such as czs-2-amino-2-methylcyclopentanecarboxylic acid [56], m-2-amino-2-methylcyclo-hexanecarboxylic acid [56], (l/ , 2S, 4S )2-amino-4-terMnitylcyclopenta-necarboxylic acid [55, 58], 3-exo-aminobicyclo[2.2.1]heptane-2-exo-carboxylic acid [59, 60] and 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid [61]. 

Various enantioselective syntheses of homologue and analogue derivatives of 2-ACPC have been described, for example in refs. [100-109]. 

A number of further transformations of homologue and analogue alicyclic amino alcohols have been performed, resulting in various heterocyclic compounds [117, 152-166]. 

Jonsson KO, Vandevoorde S, Lambert DM, Tiger G, and Fowler CJ (2001) Effects of homologues and analogues of palmitoylethanolamide upon the inactivation of the endocannabinoid anandamide. Br J Pharmacol 133 1263-75. 

Owen s detailed descriptions of homology and analogy, as opposed to the stark definitions of homologue and analogue, appeared in his Archetype and Homologies of the Vertebrate... 

I identified three milestones in the development of the concept of homology (1) Owen s distinction and clarification of homology and analogy (and homologue and analogue), (2) Patterson s distinction between taxic and transformational homology, and (3) Nelson s introduction of the concept of relationship into studies of homology. 

Boyden, A., Homology and analogy a century after the definitions of homologue and analogue of Richard Owen, Quarterly Rev. Biol., 18, 228-241, 1943. 

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