4221-03-8Relevant articles and documents
INTRAMOLECULAR DIELS-ALDER REACTIONS OF ETHYL 2,4,9-DECATRIENOATE AND 2,4,10-UNDECATRIEONATE
Lin, Yi-Tsong,Houk, K. N.
, p. 2517 - 2520 (1985)
The title compounds undergo intramolecular Diels-Alder reactions at 180 deg C to give ester-substituted hydrindane and decalin ring systems, with trans/cis ratios of 43:57 and 50:50, respectively.
Quinolinium Bichromate Oxidation of Diols: A Kinetic Study
Kuotsu, Bernadette,Tiewsoh, Enboklin,Debroy, Abhijit,Mahanti, Mahendra K.
, p. 8875 - 8877 (1996)
Quinolinium dichromate (QDC) in water oxidizes vicinal and nonvicinal diols to the corresponding α-hydroxy carbonyl compound. The rate is proportional to the concentrations of diol, oxidant and hydrogen ions, and the reactions proceed almost twice as fast in D2O than in H2O. These data can be correlated with a mechanistic pathway involving the intermediate formation of a chromate ester, which undergoes decomposition to give the product.
Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation
Mukherjee, Aparajita,Bhattacharya, Samaresh
, p. 15617 - 15631 (2021/05/19)
The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.
Influence of Some Factors on the Progress of a New Reaction in the Chemistry of Organoaluminum Compounds
Ishmuratov, G. Yu.,Vydrina, V. A.,Yakovleva, M. P.
, p. 1353 - 1358 (2020/10/02)
Abstract: We earlier discovered a new reaction in the chemistry of organoaluminum compounds (OACs), specifically, the formation of O-isobutyl acetals on low-temperature (–70°C) treatment of seven-membered lactones with a double (or more) molar amount of diisobutylaluminum hydride (DIBAH) in methylene chloride. To assess the boundaries for the formation of isobutyl acetals depending on the ring size, we involved in the low-temperature hydride reduction six-, eight-, and thirteen-membered lactones. To determine how the scope of the new reaction depends on the nature of the organoaluminum reagent, we tested triisobutylaluminum (TIBA). To determine how the formation of isobutyl acetals on low-temperature (–70°C) reduction with excess DIBAH in CH2Cl2 depends on whether the starting ester is cyclic or acyclic and, if the former is the case, on the ring size in the ester, we used the acyclic methyl octadecanoate as the starting compound. It was found that the new reaction in the chemistry of AOC with DIBAH as the reducer is characteristic only of seven-membered lactones and atypical of acyclic methyl octadecanoate and ricinoleate (i.e. acids with the carbon chain length more than 6).
Transiently Thermoresponsive Acetal Polymers for Safe and Effective Administration of Amphotericin B as a Vaccine Adjuvant
Van Herck, Simon,Van Hoecke, Lien,Louage, Benoit,Lybaert, Lien,De Coen, Ruben,Kasmi, Sabah,Esser-Kahn, Aaron P.,David, Sunil A.,Nuhn, Lutz,Schepens, Bert,Saelens, Xavier,De Geest, Bruno G.
, p. 748 - 760 (2017/12/18)
The quest for new potent and safe adjuvants with which to skew and boost the immune response of vaccines against intracellular pathogens and cancer has led to the discovery of a series of small molecules that can activate Toll-like receptors (TLRs). Whereas many small molecule TLR agonists cope with a problematic safety profile, amphotericin B (AmpB), a Food and Drug Administration approved antifungal drug, has recently been discovered to possess TLR-triggering activity. However, its poor aqueous solubility and cytotoxicity at elevated concentrations currently hampers its development as a vaccine adjuvant. We present a new class of transiently thermoresponsive polymers that, in their native state, have a phase-transition temperature below room temperature but gradually transform into fully soluble polymers through acetal hydrolysis at endosomal pH values. RAFT polymerization afforded well-defined block copolymers that self-assemble into micellar nanoparticles and efficiently encapsulate AmpB. Importantly, nanoencapsulation strongly reduced the cytotoxic effect of AmpB but maintained its TLR-triggering capacity. Studies in mice showed that AmpB-loaded nanoparticles can adjuvant an RSV vaccine candidate with almost equal potency as a highly immunogenic oil-in-water benchmark adjuvant.
