110352-23-3

Upstream product

• 81370-49-2 cyclotriguaiacyclene 
• 81329-97-7 [3-methyloxy-4-(2-iodoethoxy)phenyl]methanol 
• 81329-95-5 2,7,12-Tris-(2-iodo-ethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene 
• 162060-76-6 (+/-)-2,7,12-Tris(2-hydroxyethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 
• 1311229-15-8 C₅₄H₅₄O₁₅ 
• 81329-96-6 (+/-)-2,7,12-Tris(ethoxymethanesulfonate)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 
• 81342-18-9 (+/-)-2,7,12-Tris(methoxycarbonylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 

Downstream Products

• 112018-90-3 cryptophane-A 

Relevant academic research and scientific papers

Synthesis of a (D3)-Bis(cyclotriveratrylenyl) Macrocage by Stereospecific Replication of a (C3)-Subunit

(D3)-Bis(cyclotriveratrylenyl) (4), has been synthesized in racemic and optically active forms by stereospecific replication of a (C3)-subunit; the absolute configuration of (+)-(4) was assigned from that of the (C3)-precursor.

Access to the Syn diastereomers of cryptophane cages using HFIP

Cryptophane cages can adopt either an anti or syn configuration that present different recognition properties. While the synthesis of anti-cryptophanes is well reported, the synthesis of syn-cryptophanes remains a challenge. Herein, we demonstrate that the use of HFIP as a co-solvent during the second ring closure reaction significantly affects the regioselectivity, providing easier access to the syn-cryptophane stereomers.

Synthesis and Exciton Optical Activity of D3-Cryptophanes

Six optically active D3-cryptophanes (1-6) have been synthesized and thei absolute configurations established unambiguously.In order to explain their circular dichroism (CD) spectra, a simple theoretical model, based on the Kuhn-Kirkwood excition mechanism, has been developed for the coupling of six equivalent oscillators in a D3 molecular point group.The model predicts for each B2u and B1u benzene transition the presence of three CD components, one (A2) being polarized along the C3 axis and two (E) in the plane containing the C2 axes.The two E components have opposite signs and different intensities, the stronger having sign opposite to the A2 transition.The splitting between the E states in each band system is dependent on the twist angle (2γ) between the upper and the lower caps of the molecule.For 2γ = 60 deg (staggered conformation), this splitting is estimated to be very small, compared to the corresponding E - A2 energy difference, and the E components are never resolved in the theoretical plotted spectra for any realistic bandwith.For 2γ = 0 deg (eclipsed conformation), the calculated splitting of the E states is large enough to become apparent in plotted spectra for the B1u system.When a staggered conformation is assumed, the experimental CD spectra of cryptophanes 1-6 have been, in most cases, satisfactorily interpreted in terms of the model, with the polarization direction of the transitions set in accordance to the spectroscopic moment theory by using the rules previouly established for C3-cyclotriveratrylenes.In some cases, the energy sequence of the E states for the B2u system is not agreement with the predictions, probably due to the failure of the point-dipole approximation to determine the exact sequence of almost degenerate states.The results of this study point out the importance of the coupled-oscillator model in explaining the CD spectra of complex molecules containing more than three oscillators.