109214-69-9

Upstream product

• 109087-15-2 cis-2-hydroxymethylcyclohexylamine 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 142892-61-3 ((1R,2S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-methanol 
• 107832-25-7 N-(4-Chlorbenzyl)-cis-2-(hydroxymethyl)-1-cyclohexylamin 
• 142892-61-3 ((1S,2S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-methanol 
• 107832-25-7 N-(4-Chlorbenzyl)-trans-2-(hydroxymethyl)-1-cyclohexylamin 

Relevant academic research and scientific papers

Formation of 3,1-Perhydrobenzoxazines and their N-Methyl Derivatives. The Effects of Epimerization and Temperature

The cyclization reactions of p-nitrobenzaldehyde with cis- and trans-2-hydroxy-methylcyclohexylamine and of their N-methyl derivatives have been studied by 1H NMR spectroscopy in CDCl3 solution.Time-dependent spectra confirmed that the reactions with both cyclohexylamines proceeded via open-chain intermediates whereas those with the N-methyl derivatives showed no signs of such intermediates.In all but one case the thermodynamically more stable 3,1-perhydrobenzoxazine epimer was also the kinetically favoured product.The effects of temperature and the presence of the minor epimer on the ring-chain tautomeric equilibria are also discussed.

Ring-Chain Tautomerism in 1,3-Oxazines

A comparative study on the ring-chain tautomerism of 49 2-(substituted-phenyl) tetrahydro-1,3-oxazines of seven different types, namely, tetrahydro-1,3-oxazines 3,r-8a,c-2,c-4a- and r-8a,c-2,t-4a-1,3-perhydrobenzoxazines 5 and 7,r-8a,c-2,c-4- and r-8a,c-2,t-4a-1,3-perhydrobenzoxazines 9 and 11, 3,4-dihydro-2H-1,3-benzoxazines 12, and 1,2-dihydro-4H-3,1-benzoxazines 13, pointed out that in all cases the equilibria can be described with a simple equation, log Kx = (0.76 +/- 0.04)?+ + logKX=H where Kx = /(X/H).A factor c illustrating the sum of ster ic and electronic effects of substituents at C-4,C-5, and C-6 has also been introduced

STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES

The cis- and trans-2-amino-4-cyclohexene-1-carboxylic acids 1 and 3 react with imidates to give the condensed-skeleton, bicyclic cis- and trans-pyrimidin-4-ones 8 and 9.The amino acids 1 and 3 were reduced to the cis- and trans-1,3-aminoalcohols 6 and 7, which were cyclized by means of imidates to the bicyclic tetrahydro-4H-3,1-benzoxazines 10 and 11, or were converted, via the corresponding carbamates 14 and 15 into the tetrahydro-4H-3,1-benzoxazin-2(1H)-ones 16 and 17.The 2-thioxo analogues 18 and 19 were prepared by cyclization of the dithiocarbamates obtained from the aminoalcohols 6 and 7 by treatment with carbon disulphide.The trans-aminoalcohol 7 and its saturated analogue reacted with p-chlorobenzaldehyde to furnish the hexahydro 13 and octahydro-4H-3,1-benzoxazine 13a, respectively. 1H and 13C NMR studies showed that, similarly to the earlier-investigated analogues containing oxygen or unsubstituted nitrogen at position 1, the synthesized cis isomers 8, 10, 16 and 18 occurred as the preferred conformer in the heterocyclic twist inverse form of N-inside type (quasiaxal C6-N bond) (B).In the trans isomers containing a saturated C-2 atom (13 and 13a), H-2 and H-6 are in cis relative positions.