67106-71-2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 767-00-0 4-cyanophenol 
• 694-54-2 tetrahydro-2H-2-pyranol 

Downstream Products

• 875708-42-2 4-tetrahydropyranyloxybenzylamine 
• 104575-16-8 4-<2-(diethylamino)ethoxy>-4'-<(tetrahydropyran-2-yl)oxy>benzophenone 
• 104575-12-4 (Z)-1-{4-[2-(diethylamino)ethoxy]phenyl}-1-(4-hydroxyphenyl)-2-phenylethene 
• 104575-21-5 (E)-1-<4-<2-(diethylamino)ethoxy>phenyl>-1-(4-hydroxyphenyl)-2-phenylethene 
• 104575-13-5 (Z)-2-phenyl-3-(4-hydroxyphenyl)-3-<4-<2-(diethylamino)ethoxy>phenyl>acrylonitrile 
• 104575-22-6 (E)-2-phenyl-3-<4-<2-(diethylamino)ethoxy>phenyl>-3-(4-hydroxyphenyl)acrylonitrile 
• 1026750-87-7 C₃₂H₃₆N₄O₈ 
• 1027047-37-5 C₃₂H₃₆N₄O₈ 
• 188922-40-9 C₃₃H₃₈N₄O₈ 
• 1026945-77-6 C₂₉H₃₁N₃O₆ 
• 188922-39-6 N,N'-bis(benzyloxycarbonyl)-N''-4-hydroxybenzylguanidine 

Relevant academic research and scientific papers

Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

Benzylguanidines and other galegine analogues inducing weight loss in mice

Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; ± SEM) of -19.7 ± 1.0, -11.0 ± 0.7, and -7.3 ± 0.8 in BALB/c, ob/ob, and DIO models, respectively.

Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading

This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state. Georg Thieme Verlag Stuttgart.

Reaction of tetrahydropyranyl ethers with triethylsilyl trifluoromethanesulfonate-2,4,6-collidine combination: Speculation on the intermediate, efficient deprotection, and application to efficient ring-closing metathesis as a tether

The reaction of tetrahydropyranyl (THP) ethers with triethylsilyl trifluoromethanesulfonate (TESOTf)-2,4,6-collidine proceeded via collidinium salt intermediates to give the alcohol and 4-triethylsiloxybutanal in good yields. The structure of the intermediate was confirmed by 1HNMR and FAB-MS studies and by trapping it with EtOH. The reaction was applied for mild, efficient, and highly chemoselective deprotection method of THP ethers. The characteristic feature of the reaction is that the reaction conditions are weakly basic. Then, the reaction can proceed without affecting acid-labile protecting groups. Furthermore, the intermediates from alkenol-THP ether were trapped with other alkenols to give acyclic mixed acetals, which were subjected to efficient ring-closing metathesis by using the tetrahydropyranyl unit as a tether.

Selective tetrahydropyranylation under non-acidic conditions

We report that the tetrahydropyranylation of hydroxyl groups, exhibiting especially very low nucleophilicities, can be achieved by means of Mitsunobu reaction with 2-hydroxytetrahydropyran. This reaction led to the protection of phenols and pyridinols without the use of an acidic catalyst. For instance hydroxypyridines could not be protected by dihydropyran under acidic conditions, whereas they underwent a smooth tetrahydropyranylation under Mitsunobu conditions. The method is selective for a phenol over an alcohol. Georg Thieme Verlag Stuttgart.

Tetrahydropyranylation of alcohols, thiols, phenols and primary amines catalysed by magnesium halide

An efficient and mild method for tetrahydropyranylation of thiols, alcohols, phenols and primary amines using a catalytic amount of MgX 2 (X = Br or I) is described; due to the neutral conditions employed, the method is also compatible with com

Enzymatic peptide synthesis with p-guanidinophenyl and p- (guanidinomethyl)phenyl esters as acyl donors

Two series of 'inverse substrates', N-Boc-amino acid p-guanidinophenyl and p-(guanidinomethyl)phenyl esters, were prepared as acyl donor components for enzymatic peptide synthesis. The kinetic behavior of these esters toward bovine and Streptomyces griseus (SG) trypsin was analyzed. The spatial requirement of the active site of these enzymes for catalytic efficiency is discussed based on the steric characteristics of the substrates. These substrates were found to couple readily with amino acid p-nitroanilides to produce peptides. SG trypsin was the most efficient catalyst among the enzymes tested (bovine, porcine, and SG trypsin).

The conformational behaviour of 2-aryloxytetrahydropyrans and 2-acetoxytetrahydropyran, and barrier to ring inversion

The 13C nuclear magnetic resonance data of a series of 2-(4-substituted-phenoxy)tetrahydropyrans at 156 K and in CF2Br2 and CHFCl2 solvents show that the axial preference increases with electron withdrawal in the aryloxy group: from 79 percent (ΔG0E->A = -0.4 kcal mol-1) (4-OCH3) to 90 percent (ΔG0E->A = -0.7 kcal mol-1) (4-NO2) in CF2Br2.The axial preference (anomeric effect) is smaller in the more polar CHFCl2 solvent, as expected, and the substituent effect is smaller also: change in ΔG0E->A from -0.3 (4-OCH3) to -0.5 (4-NO2) kcal mol-1.However, the axial preference of 2-acetoxytetrahydropyran is shown to be smaller than that of 2-phenoxytetrahydropyran in CF2Br2 solvent although the acetoxy group is expexted to be more electronegative than the phenoxy group.Furthermore, the polarity of the solvent has no effect on the conformational equilibrium of 2-acetoxytetrahydropyran.The results are interpreted in terms of both orbital and electrostatic interactions.The ring-inversion barrier of 2-alkoxy and 2-aryloxytetrahydropyrans, determined by the temperature-coalescence method, is lower than that of tetrahydropyran by about 1.5 kcal mol-1.