847018-76-2

Upstream product

• 112-54-9 Dodecanal 
• 108-46-3 recorcinol 
• 120-80-9 benzene-1,2-diol 
• 1191-99-7 2,3-dihydro-2H-furan 

Downstream Products

• 196860-34-1 (17s,18s,19s,20s)-17,18,19,20-tetraundecyl-3⁴,3⁵,7⁴,7⁵,11⁴,11⁵,15⁴,15⁵-octanitro-2,4,6,8,10,12,14,16-octaoxa-3,7,11,15(1,2),1,5,9,13(1,2,4,5)-octabenzenapentacyclo[11.3.1.1^1,5.1^5,9.1^9,13]icosaphane 
• 935537-58-9 C₁₀₀H₁₂₀Br₈O₈ 
• 252684-36-9 Tiiii[C₁₁H₂₃,H,Ph] 
• 1242059-68-2 4,6,10,12,16,18,22,24-octahydroxy-5-[3,5-di(tert-butyl)-4-hydroxybenzyl]-2,8,14,20-tetranonylpentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1⁽²⁵⁾,3,5,7⁽²⁸⁾,9,11,13⁽²⁷⁾,15,17,19⁽²⁶⁾,21,23-dodecaene 

Relevant academic research and scientific papers

Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ-Selinene and Mechanistic Studies

The synthesis of terpene natural products remains a challenging task due to the enormous structural diversity in this class of compounds. Synthetic catalysts are unable to reproduce the tail-to-head terpene cyclization of cyclase enzymes, which create this diversity from just a few simple linear terpene substrates. Recently, supramolecular structures have emerged as promising enzyme mimetics. In the present study, the hexameric resorcinarene capsule was utilized as an artificial cyclase to catalyze the cyclization of sesquiterpenes. With the cyclization reaction as the key step, the first total synthesis of the sesquiterpene natural product δ-selinene was achieved. This represents the first total synthesis of a sesquiterpene natural product that is based on the cyclization of a linear terpene precursor inside a supramolecular catalyst. To elucidate the reaction mechanism, detailed kinetic studies and kinetic isotope measurements were performed. Surprisingly, the obtained kinetic data indicated that a rate-limiting encapsulation step is operational in the cyclization of sesquiterpenes.

Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies

The tail-to-head terpene cyclization is arguably one of the most complex reactions found in nature. The hydrogen-bond-based resorcinarene capsule represents the first man-made enzyme-like catalyst that is capable of catalyzing this reaction. Based on noncovalent interactions between the capsule and the substrate, the product selectivity can be tuned by using different leaving groups. A detailed mechanistic investigation was performed to elucidate the reaction mechanism. For the cyclization of geranyl acetate, it was found that the cleavage of the leaving group is the rate-determining step. Furthermore, the studies revealed that trace amounts of acid are required as cocatalyst. A series of control experiments demonstrate that a synergistic interplay between the supramolecular capsule and the acid traces is required for catalytic activity.

Halogen Bonding Molecular Capsules

Molecular capsules based solely on the interaction of halogen bonding (XB) are presented along with their host-guest binding properties in solution. The first example of a well-defined four-point XB supramolecular system is realized by decorating resorcin[4]arene cavitands with polarized halogen atoms for dimerization with tetra(4-pyridyl) resorcin[4]arene cavitands. NMR binding data for the F, Cl, Br, and I cavitands as the XB donor show association constants (Ka) of up to 5370 M-1 (ΔG283 K=-4.85 kcal mol-1, for I), even in XB-competitive solvent, such as deuterated benzene/acetone/methanol (70:30:1) at 283 K, where comparable monodentate model systems show no association. The XB capsular geometry is evidenced by two-dimensional HOESY NMR, and the thermodynamic profile shows that capsule formation is enthalpically driven. Either 1,4-dioxane or 1,4-dithiane are encapsulated within each of the two separate cavities within the XB capsule, with of up to Ka=9.0 108 M-2 (ΔG283 K=-11.6 kcal mol-1).

Pore formation in phospholipid bilayers by amphiphilic cavitands

Five new cavitands were prepared that have four pendant n-undecyl chains and "headgroups" connected by 2-carbon spacers. The headgroups were ～OCH2CONH-Ala-OCH3, 1; ～OCH2CONH-Phe- OCH3, 2; ～OCH2CONH-Ala-OH, 3; ～OCH 2CONH-Phe-OH, 4; and ～OCH2CONHCH2CH 2-thyminyl, 5. Pore formation by each cavitand was studied by use of the planar bilayer conductance experiment. All five compounds were found to form pores in asolectin bialyer membranes. Compounds 1-3 behaved in a generally similar fashion and exhibited open-close dynamics. Compounds 4 and 5 formed pores more rapidly, were more dynamic, and led more quickly to membrane rupture. Differences in the ion transport activity are rationalized in terms of structure and aggregate cavitand assemblies.

The absolute configuration of an inherently chiral phosphonatocavitand and its use toward the enantioselective recognition of L-adrenaline

An inherently chiral ABii diphosphonato cavitand (±)-4 bearing a single quinoxaline bridging moiety was synthesized and resolved by chiral HPLC. Its chiroptical properties were investigated and VCD experiments allowed the determination of its absolute con

Serendipity in the crystallization of a series of C-alkylcalix[4] resorcinarenes from alcoholic solvents

The crystal structures of a series of C-alkylcalix[4]resorcinarenes (alkyl = methyl, propyl, butyl, pentyl, hexyl, heptyl, and undecyl), each crystallized from tert-butanol, are reported. In all seven of these structures, eight tert-butanol molecules link two resorcinarenes with 16 hydrogen bonds, thereby facilitating the formation of simple dimeric hydrogen-bonded capsules, each of which encapsulates one (disordered) tert-butanol molecule as guest. These structures are compared with, and contrasted to, those obtained from the same series of resorcinarenes recrystallized both from mixed solvents containing tert-butanol and from methanol alone.

Monomeric, dimeric and hexameric resorcin[4]arene assemblies with alcohols in apolar solvents

Resorcin[4]arenes in an apolar solvent containing alcohols exist in three forms of self-assembled aggregates which have been characterised by the technique of diffusion NMR spectroscopy. The Royal Society of Chemistry.

Synthesis and cubic nonlinear optical behavior of phenyl and ferrocenyl-ended resorcinarene-based dendrimers

Dendrimers were synthesized with phenyl and ferrocenyl-ended groups joined by vinyl moieties. All the dendrons used for dendrimers synthesis had showed trans configuration. This configuration as well as the 'cone' conformation of the resorcinarenes was preserved in the dendrimers, as it was shown by 1H NMR spectroscopy. The chemical structure and purity of the synthesized dendrimers were confirmed by 1H and 13C NMR, FAB+, MALDI-TOF, electrospray mass spectra, and elemental analysis. Cubic nonlinear optical behavior of this first generation of resorcinarene dendrimers was studied. The χ(3) values estimated from the THG Maker-fringe technique for the phenyl and ferrocenyl-ended resorcinarene dendrimers dispersed in thin solid films are of the order of 10-13 and 10-12 esu, respectively.

Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer

Resorcinarenes were functionalized with fluorophores and fluorescence resonance energy transfer (FRET) was employed as a tool to probe the dynamic behavior of hydrogen-bonded hexameric assemblies at nanomolar concentrations. The encapsulation of a fluorescent guest inside the capsule made it possible to observe FRET across the mechanical boundary of the hexameric assembly. Copyright

Selective steroid recognition by a partially bridged resorcin[4]arene cavitand

The partially bridged resortin[4]arene cavitand 1 featuring a cleft-shaped recognition site formed by two anti-quinoxaline bridges and four convergent HO-groups was prepared in three steps and characterised by X-ray crystallography; cavitand 1 was found to be a selective receptor for steroidal substrates in CDCl3, with the best binding observed for steroids with a flat A-ring and two H-bonding sites on rings A and C/D. The Royal Society of Chemistry 2005.