23294-55-5Relevant academic research and scientific papers
Iridium-catalysed primary alcohol oxidation and hydrogen shuttling for the depolymerisation of lignin
Lancefield, Christopher S.,Teunissen, Lucas W.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.
, p. 3214 - 3221 (2018/07/31)
Lignin is a potentially abundant renewable resource for the production of aromatic chemicals, however its selective depolymerisation is challenging. Here, we report a new catalytic system for the depolymerisation of lignin to novel, non-phenolic monoaromatic products based on the selective β-O-4 primary alcohol dehydrogenation with a Cp?Ir-bipyridonate catalyst complex under basic conditions. We show that this system is capable of promoting the depolymerisation of model compounds and isolated lignins via a sequence of selective primary alcohol dehydrogenation, retro-aldol (Cα-Cβ) bond cleavage and in situ stabilisation of the aldehyde products by transfer (de)hydrogenation to alcohols and carboxylic acids. This method was found to give good to excellent yields of cleavage products with both etherified and free-phenolic lignin model compounds and could be applied to real lignin to generate a range of novel non-phenolic monomers including diols and di-acids. We additionally show, by using the same catalyst in a convergent, one-pot procedure, that these products can be selectively channelled towards a single di-acid product, giving much simpler product mixtures as a result.
Copolymerization of lactones and bioaromatics: Via concurrent ring-opening polymerization/polycondensation
Nguyen, Ha Thi Hoang,Short, Gabriel N.,Qi, Pengxu,Miller, Stephen A.
supporting information, p. 1877 - 1888 (2017/06/09)
The general and efficient copolymerization of lactones with hydroxy-acid bioaromatics was accomplished via a concurrent ring-opening polymerization (ROP) and polycondensation methodology. Suitable lactones were l-lactide or ε-caprolactone and four hydroxy-acid comonomers were prepared as hydroxyethyl variants of the bioaromatics syringic acid, vanillic acid, ferulic acid, and p-coumaric acid. Copolymerization conditions were optimized on a paradigm system with a 20 : 80 feed ratio of caprolactone : hydroxyethylsyringic acid. Among six investigated catalysts, polymer yield was optimized with 1 mol% of Sb2O3, affording eight copolymer series in good yields (32-95% for lactide; 80-95% for caprolactone). Half of the polymers were soluble in the GPC solvent hexafluoroisopropanol and analyzed to high molecular weight, with Mn = 10 500-60 700 Da. Mass spectrometry and 1H NMR analysis revealed an initial ring-opening formation of oligolactones, followed by polycondensation of these with the hydroxy-acid bioaromatic, followed by transesterification, yielding a random copolymer. By copolymerizing bioaromatics with l-lactide, the glass transition temperature (Tg) of polylactic acid (PLA, 50 °C) could be improved and tuned in the range of 62-107 °C; the thermal stability (T95%) of PLA (207 °C) could be substantially increased up to 323 °C. Similarly, bioaromatic incorporation into polycaprolactone (PCL, Tg = -60 °C) accessed an improved Tg range from -48 to 105 °C, while exchanging petroleum-based content with biobased content. Thus, this ROP/polycondensation methodology yields substantially or fully biobased polymers with thermal properties competitive with incumbent packaging thermoplastics such as polyethylene terephthalate (Tg = 67 °C) or polystyrene (Tg = 95 °C).
COMPOUNDS FOR THE TREATMENT OF PARAMOXYVIRUS VIRAL INFECTIONS
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Paragraph 0586, (2014/03/25)
Disclosed herein are new antiviral compounds, together with pharmaceutical compositions that include one or more antiviral compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a paramyxovirus viral infection with one or more small molecule compounds. Examples of paramyxovirus infection include an infection caused by human respiratory syncytial virus (RSV).
Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part I: Discovery of 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide
Uto, Yoshikazu,Ogata, Tsuneaki,Harada, Jun,Kiyotsuka, Yohei,Ueno, Yuko,Miyazawa, Yuriko,Kurata, Hitoshi,Deguchi, Tsuneo,Watanabe, Nobuaki,Takagi, Toshiyuki,Wakimoto, Satoko,Okuyama, Ryo,Abe, Manabu,Kurikawa, Nobuya,Kawamura, Sayako,Yamato, Michiko,Osumi, Jun
scheme or table, p. 4151 - 4158 (2010/04/29)
A series of structurally novel stearoyl-CoA desaturase-1 (SCD-1) inhibitors has been identified by optimizing a hit from our corporate library. Preliminary structure-activity relationship (SAR) studies led to the discovery of the highly potent and orally bioavailable thiazole-based SCD-1 inhibitor, 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (23a).
