38628-53-4Relevant academic research and scientific papers
Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
, p. 3583 - 3588 (2020/08/05)
Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
Sulfur-containing compound based on glutaryl imide skeleton and application of compound
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Paragraph 0167; 0585-0586, (2020/09/12)
The present disclosure relates to compound shown in a formula (I) or salts, solvates, isotope-enriched analogs, tautomers, polymorphs, stereoisomers, or mixtures of stereoisomers of the compound, andthe application thereof in the treatment of tumours. The present disclosure also provides tumor treatment application of the compound showed in a formula (I') or pharmaceutically acceptable salts, solvates, isotope-enriched analogs, tautomers, polymorphic substances, stereoisomers, or mixtures of stereoisomers of the compound.
Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction
Crespi, Stefano,Donabauer, Karsten,K?nig, Burkhard,Murugesan, Kathiravan,Rozman, Ur?a
supporting information, p. 12945 - 12950 (2020/09/23)
A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.
Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
Aleku, Godwin A.,Leys, David,Roberts, George W.
, p. 3927 - 3939 (2020/07/09)
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions
Read, Christopher D. G.,Moore, Peter W.,Williams, Craig M.
, p. 4537 - 4540 (2015/09/15)
N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.
Selective oxidations of activated alcohols in water at room temperature
Lipshutz,Hageman,Fennewald,Linstadt,Slack,Voigtritter
, p. 11378 - 11381 (2014/11/08)
Allylic and benzylic alcohols can be selectively oxidized to their corresponding aldehydes or ketones in water containing nanoreactors composed of the designer surfactant TPGS-750-M. The oxidation relies on catalytic amounts of CuBr, bpy, and TEMPO, with N-methyl-imidazole; air is the stoichiometric oxidant. the Partner Organisations 2014.
Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis
Kuwano, Satoru,Harada, Shingo,Oriez, Raphael,Yamada, Ken-Ichi
supporting information; experimental part, p. 145 - 147 (2012/01/12)
Depending on the N-heterocyclic carbene catalyst utilized, α-unbranched aldehydes selectively provided amides, esters, or carboxylic acids through oxidation by NCS. The α-unbranched aldehyde underwent these reactions chemoselectively in the presence of an aromatic or α-branched aldehyde.
NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS
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, (2011/10/01)
The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
Chemical constituents of Parkia javanica, Alocasia indica and Premna latifolia
Dinda,Mohanta,Ghosh,Sato,Harigaya
body text, p. 829 - 831 (2011/04/22)
Isolation and characterization of one new phenyl propanoid, parkinol from Parkia javanica leaves; five known sterols, ergosterol, campesterol, stigmasterol, β-sitosterol and clionasterol from Alocasia indica tubers; and two known sterols, β-sitosterol and stigmasterol from Premna latifolia leaves are reported. The structure of parkinol was established as 4′ (methylene nonanoyloxy)-3-phenyl propanol by spectroscopic studies.
Paracyclophanes: Extending the bridges. Synthesis
Pechlivanidis, Zissis,Hopf, Henning,Ernst, Ludger
experimental part, p. 223 - 237 (2009/06/21)
Preparatively satisfactory routes to [3.2]paracyclophane (10), [4.2]paracyclophane (14), [4.3]paracyclophane (19) as well as several derivatives of these compounds - among others the bromides 25, the ester 31, the diesters 40-43 - are described using well-established methods of cyclophane chemistry (ring-closure reactions leading to thiacyclophanes, ring contraction by sulfone pyrolysis). The parent systems and their derivatives are now available in gram quantities allowing a study of their chemical properties. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
