65550-19-8

Upstream product

• 65550-20-1 methyl 3-allyloxy-2-naphthoate 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 106-95-6 allyl bromide 
• 7163-25-9 ethyl 3-hydroxy-2-naphthanoate 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 581-71-5 2-Hydroxy-3-naphthaldehyde 

Downstream Products

• 65550-18-7 4-allyl-3-hydroxy-2-naphthoic acid 

Relevant academic research and scientific papers

Ester-linked alkyl chain effect on the 2D structures of isobutenyl compounds: Scanning tunneling microscopic study

Various lengths of alkyl chains were introduced to the basic skeleton of isobutenyl ether compounds via ester bond (D1-OCn), and the 2D structures were investigated by using scanning tunneling microscopy at a solid/liquid interface. In the D1-OCn, two naphthalene units with ester-linked alkyl chains were connected with the isobutenyl group. The D1-OCnpossessing C18-21 alkyl chains displayed alternate changes in the 2D structures, in which the alkyl chains were oriented in the same direction to form an interdigitation, whereas those with C15-17 chains showed the same dumbbell-shaped structures, suggesting that there is a specific alkyl chain length range exhibiting the odd-even effect. After the thermal reaction of tandem Claisen rearrangement (TCR), ether functions in the D1-OCn were converted to hydroxy groups accompanied by a new C-C bond formation (D2-OCn). Then, odd-even effect in the D1-OCn was completely cancelled to show only linear alignment in which the alkyl chains turned to the opposite direction, regardless of the alkyl chain length in the rearranged compounds (D2-OCn). This result indicates that various 2D structures of the isobutenyl compounds with ester groups can be transformed to the same linear alignment by the TCR. However, odd-even effect and structural transformation due to the Claisen rearrangement were unavailable for the "half" molecule containing a single naphthalene unit with an alkyl chain and an allyl moiety. Therefore, it can be concluded that dual alkyl chains connected to the naphthalene units are necessary for the isobutenyl ether compounds to reveal the odd-even effect and structural transformation by the TCR.

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Repurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (Ki 50 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys25 to a sulfenic acid (Cys-SOH) during crystallization. The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined. When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs 13.0 for untreated controls) mean days of survival.

Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.

THE CLAISEN REARRANGEMENT OF SOME ALLYL-β-NAPHTHYL ETHERS AND CYCLIZATION OF THE PRODUCTS

Some allyl-2-carboxy-3-hydroxy- as well as 2,3- and 2,7-diallyloxynaphtalenes were obtained.Respectively rearranged compounds were cyclized to naphthodihydrofuran rings.