3762-25-2Relevant articles and documents
Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction
Beletskaya, Irina P.,Titanyuk, Igor D.
, p. 2748 - 2757 (2022/03/14)
The simple synthetic procedure for preparation of α-aryl-α-diazophosphonates via a diazo transfer reaction is proposed. Benzylphosphonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in a yield up to 79%. The proposed method is general. The reaction uses easily available starting materials, tolerates various functional groups, and may be applied for multi-gram scale synthesis.
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups
Cao, Chao-Tun,Yan, Lu,Cao, Chenzhong
, (2021/05/21)
Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.
Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins
Decker, Luka J. B.,Dittgen, Jan,Frackenpohl, Jens,Freigang, J?rg,Génix, Pierre,Helmke, Hendrik,Lange, Gudrun,Luemmen, Peter,Schmidt, Jana,Schmutzler, Dirk,Vors, Jean-Pierre
, (2020/09/16)
New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).
Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution
Fu, Zhicheng,Sun, Simin,Yang, Anjian,Sun, Fang,Xu, Jiaxi
supporting information, p. 13124 - 13127 (2019/11/11)
A novel and transition metal-free synthesis of 3,4-dihydro-1,2-oxaphosphinine 2-oxides was developed. LiHMDS-mediated tandem Michael addition and nucleophilic substitution of readily available phosphonochloridates and chalcones afforded a variety of valuable 3,4-dihydro-1,2-oxaphosphinine 2-oxides bearing diverse functionalities in excellent yields and satisfactory to good diastereoselectivity (up to 99% yield and up to 99?:?1 dr).
Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates
Huang, Hai,Denne, Johanna,Yang, Chou-Hsun,Wang, Haobin,Kang, Jun Yong
, p. 6624 - 6628 (2018/05/14)
A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.
SUBSTITUTED OXOTETRAHYDROQUINOLINYLPHOSPHINIC ACID AND PHOSPHINIC ACID AMIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS
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Paragraph 0155-0156, (2018/08/03)
The invention relates to substituted oxotetrahydroquinolinylphosphin- and -phosphonamides of the general formula (I) and salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.
Novel preparation method of sulfonium salt derivatives with stilbene as conjugated system
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Paragraph 0056; 0057; 0059; 0065; 0066, (2018/09/21)
The invention provides a novel preparation method of sulfonium salt derivatives with stilbene as a conjugated system. The method comprises steps as follows: firstly, benzyl halides (Hal denotes halogen atom) substituted with different groups react with organic phosphate, a product reacts with benzaldehyde substituted with different sulfydryl under the alkaline condition, a high-yield disubstituted stilbene intermediate shown in (I)-a is prepared, and finally, the intermediate shown in (I)-a produces final sulfonium salt under the action of silver salt and alkyl halide or silver salt and alkyl acid ester; when different negative ions are required to be replaced, a salt exchange method is adopted to realize replacement. The provided scheme has the benefits, as examples but not confined, as follows: no noble metal catalyst is required, the raw materials are easy to obtain, and the cost is low; the reaction is performed at the room temperature, operation is simple and purification is convenient; favorable conditions are provided for large-scale industrial production of the sulfonium salt derivatives with stilbene as the conjugated system.
Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes
Deck, Lorraine M.,Whalen, Lisa J.,Hunsaker, Lucy A.,Royer, Robert E.,Vander Jagt, David L.
, p. 1423 - 1430 (2017/02/18)
Nrf2, which is a member of the cap'n’ collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation of anti-oxidant Nrf2 signaling may have therapeutic potential. A number of Nrf2 activators have entered into clinical trials. Nrf2 exists in the cytosol in complex with its binding partner Keap1, which is a thiol-rich redox-sensing protein. In response to oxidative and electrophilic stress, select cysteine residues of Keap1 are modified, which locks Keap1 in the Nrf2-Keap1 complex and allows newly synthesized Nrf2 to enter the nucleus. Numerous Nrf2-activating chemicals, including a number of natural products, are electrophiles that modify Keap1, often by Michael addition, leading to activation of Nrf2. One concern with the design of Nrf2 activators that are electrophilic covalent modifiers of Keap1 is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents, influenced not only the sensitivity to activation, reflected in EC50values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2. The stilbene backbone appears to be a privileged scaffold for development of a new class of Nrf2 activators.
Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers
Zhou, Xu,Huang, Jing,Barr, Kevin W.,Lin, Zhixing,Maya, Fernando,Abbott, Lauren J.,Colina, Coray M.,Svec, Frantisek,Turner, S. Richard
, p. 42 - 48 (2015/01/30)
Hypercrosslinked polymers containing functionalized alternating copolymer sequences of substituted stilbene or styrene and N-aryl substituted maleimides have been synthesized. Alternating copolymers containing these comonomers possess semi-rigid structures, and incorporation of these units into the precursor polymer particles for hypercrosslinking leads to a systematic increase in Tg and chain stiffness of these materials as the concentration of the comonomers is increased. Surface area and porosity of the subsequent hypercrosslinked polymers were investigated using nitrogen adsorption/desorption isotherms at 77 K. These hypercrosslinked polymers exhibit BET surface areas ranging from 1058 m2/g at 25 mol% alternating copolymer incorporation down to loss of measurable surface area at ca. 60% incorporation. The experimental surface area results correlate with predictions from simulations and serve as model systems for future studies on specifically functionalized hypercrosslinked polymer particles.
