169968-84-7

Upstream product

• 343335-76-2 (1R,2S,5R)-menthyl 4-benzyloxybenzoate 
• 2216-51-5 (-)-menthol 
• 1711-02-0 4-iodobenzoic acid chloride 
• 165557-64-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-iodobenzoate 
• 99-96-7 4-hydroxy-benzoic acid 
• 1486-51-7 p-(benzyloxy)benzoic acid 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 56441-55-5 ethyl 4-(benzyloxy)benzoate 

Downstream Products

• 343335-73-9 4-[(1R,2S,5R)-menthoxycarbonyl]phenyl phenylpropiolate 

Relevant academic research and scientific papers

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Discovery of a Small Molecule PDI Inhibitor That Inhibits Reduction of HIV-1 Envelope Glycoprotein gp120

Protein disulfide isomerase (PDI) is a promiscuous protein with multifunctional properties. PDI mediates proper protein folding by oxidation or isomerization and disrupts disulfide bonds by reduction. The entry of HIV-1 into cells is facilitated by the PDI-catalyzed reductive cleavage of disulfide bonds in gp120. PDI is regarded as a potential drug target because of its reduction activity. We screened a chemical library of natural products for PDI-specific inhibitors in a high-throughput fashion and identified the natural compound juniferdin as the most potent inhibitor of PDI. Derivatives of juniferdin were synthesized, with compound 13 showing inhibitory activities comparable to those of juniferdin but reduced cytotoxicity. Both juniferdin and compound 13 inhibited PDI reductase activity in a dose-dependent manner, with IC50 values of 156 and 167 nM, respectively. Our results also indicated that juniferdin and compound 13 exert their inhibitory activities specifically on PDI but do not significantly inhibit homologues of this protein family. Moreover, we found that both compounds can inhibit PDI-mediated reduction of HIV-1 envelope glycoprotein gp120.

Helical Disubstituted Polyacetylenes: Synthesis and Chiroptical Properties of Poly(phenylpropiolate)s

Disubstituted polyacetylenes with helical chirality have been rarely prepared due to the involved synthetic difficulty, and we here report a facile polymerization system for the synthesis of such polymers. Two groups of chiral acetylenes, i.e., C6H5C≡CCO2R* {R* = [(1S)-endo]-(-)-borneyl (1), (1R,2S,5R)-(-)-menthyl (5), cholesteryl (6)} and C6H5C≡CCO2C 6H4CO2R* [R* = borneyl (2), menthyl (3), cholesteryl (4)], are prepared by esterifications of phenylpropiolic acids with borneol, menthol, and cholesterol. Polymerizations of 1-4 are effected by WCl6-Ph4Sn, giving poly(phenylpropiolate)s P1-P4 with high molecular weights in moderate yields. The structures and properties of the polymers are characterized and evaluated by IR, UV, NMR, CD, TGA, and SEM analyses. All the polymers are stable: neither decreases in their molecular weights nor changes in their spectra are detected after the polymers have been stored on shelf for ～3 years, and no weight losses are recorded when the polymers are heated to ～300 °C. Although the polymers do not possess regioregular Z or conformations, the polyacetylene backbones are induced to helically rotate by the chiral pendants, as verified by the strong Cotton effects in the backbone absorption region of the polymers (molar ellipticity up to 102 300 deg cm2 dmol-1). The polymers exhibit helical thermochromism, with their chain helicity being continuously and reversibly tunable by temperature change. The helical polymers are capable of self-assembling, as demonstrated by the formation of twisted ribbons upon diffusing a THF solution of P3 into hexane.