cas 133730-34-4, 2,4-Dimethoxybenzeneboronic acid

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Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.
Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
p. 164 - 171
(2018/12/05)

ANTITRICHOPHYTOSIS SOLUTION FOR EXTERNAL USE
According to the present invention, a topical liquid agent having antifungal activity against dermatophytes, and further high nail permeability can be provided. The topical liquid agent for nail and/or skin for prevention or treatment of dermatophytosis comprises a film-forming agent and a compound represented by the formula: wherein R1 represents a hydrogen atom, C1-6 alkyl, or trifluoromethyl, R2 represents a hydrogen atom, C1-6 alkyl, halogen, -COO(C1-6 alkyl), or (CH2)1-3COOR where R represents a hydrogen atom or C1-6 alkyl, R3 represents a hydrogen atom, C1-6 alkyl, amino, trifluoromethyl, or OR where R represents a hydrogen atom or C1-6 alkyl, R4 represents a hydroxyl group, R5 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, or halogen, R6 represents a hydrogen atom, C1-6 alkyl, trifluoromethyl, halogen, amino, -NRaRb, nitro, hydroxy-C1-6 alkyl, -CONRaRb, -COO(C1-6 alkyl), -COOH, -(CH2)1-3COOR, or ORa where R represents a hydrogen atom or C1-6 alkyl, Ra and Rb may be the same or different from each other, and each represent a hydrogen atom, C1-6 alkyl, or C1-6 acyl, R7 represents a hydrogen atom, C1-6 alkyl, -OR where R represents a hydrogen atom or C1-6 alkyl, or halogen, R8 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, amino, or nitro, or a salt thereof.
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Paragraph 0179

(2015/07/15)

ANTI-TRICHOPHYTIC ADHESIVE PATCH
According to the present invention, a patch for nail and/or skin having antifungal activity against dermatophytes, and having higher nail permeability can be provided. The patch for nail and/or skin for prevention or treatment of dermatophytosis comprises in a pressure sensitive adhesive layer a compound represented by the formula: wherein R1 represents a hydrogen atom, C1-6 alkyl, or trifluoromethyl; R2 represents a hydrogen atom, C1-6 alkyl, halogen, -COO(C1-6 alkyl), or (CH2)1-3COOR (R represents a hydrogen atom or C1-6 alkyl); R3 represents a hydrogen atom, C1-6 alkyl, amino, trifluoromethyl, or OR (R represents a hydrogen atom or C1-6 alkyl); R4 represents a hydroxyl group; R5 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, or halogen; R6 represents a hydrogen atom, C1-6 alkyl, trifluoromethyl, halogen, amino, -NRaRb, nitro, hydroxy-C1-6 alkyl, -CONRaRb, -COO(C1-6 alkyl), -COOH, -(CH2)1-3COOR, or ORa (R represents a hydrogen atom or C1-6 alkyl, Ra and Rb may be the same or different from each other, and each represent a hydrogen atom, C1-6 alkyl, or C1-6 acyl); R7 represents a hydrogen atom, C1-6 alkyl, -OR (R represents a hydrogen atom or C1-6 alkyl), or halogen; and R8 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, amino, or nitro, or a salt thereof.
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Paragraph 0204

(2015/06/17)

PATCH FOR ANTI-DERMATOPHYTOSIS
A patch for nails or skin for prevention or treatment of dermatophytosis, containing a layer including a pressure sensitive adhesive layer and a compound represented by the formula: wherein R1 represents hydrogen, C1-16 alkyl, or trifluoromethyl; R2 represents hydrogen, C1-6 alkyl, halogen, —COO(C1-6 alkyl), or (CH2)1-3COOR; R3 represents hydrogen, C1-6 alkyl, amino, trifluoromethyl, or OR; R4 represents hydroxyl; R5 represents hydrogen, C1-6 alkyl, hydroxyl, or halogen; R6 represents hydrogen, C1-6 alkyl, trifluoromethyl, halogen, amino, —NRaRb, nitro, hydroxy-C1-6 alkyl, —CONRaRb, —COO(C1-6 alkyl), —COOH, —(CH2)1-3COOR, or ORa (Ra and Rb each represents hydrogen, C1-6 alkyl, or C1-6 acyl); R7 represents hydrogen, C1-6 alkyl, —OR, or halogen; R8 represents hydrogen, C1-6 alkyl, hydroxyl, amino, or nitro; and R represents hydrogen or C1-6 alkyl; or a salt thereof.
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Paragraph 0325; 0326

(2015/08/04)

TOPICAL LIQUID AGENT FOR THE TREATMENT OF DERMATOPHYTOSIS
A topical liquid agent for a nail and/or skin for prevention or treatment of dermatophytosis comprises a film-forming agent and a compound represented by the formula: wherein R1 represents hydrogen, C1-6 alkyl, or trifluoromethyl, R2 represents hydrogen, C1-6 alkyl, halogen, —COO(C1-6 alkyl), or (CH2)1-3COOR where R represents hydrogen or C1-6 alkyl, R3 represents hydrogen, C1-6 alkyl, amino, trifluoromethyl, or OR where R represents hydrogen or C1-6 alkyl, R4 represents hydroxyl, R5 represents hydrogen, C1-6 alkyl, hydroxyl, or halogen, R6 represents hydrogen, C1-6 alkyl, trifluoromethyl, halogen, amino, —NRaRb, nitro, hydroxy-C1-6 alkyl, —CONRaRb, —COO(C1-6 alkyl), —COOH, —(CH2)1-3COOR, or ORa where R represents hydrogen or C1-6 alkyl, Ra and Rb each represent hydrogen, C1-6 alkyl, or C1-6 acyl, R7 represents hydrogen, C1-6 alkyl, —OR where R represents hydrogen or C1-6 alkyl, or halogen, R8 represents hydrogen, C1-6 alkyl, hydroxyl, amino, or nitro, or a salt thereof.
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Paragraph 0295; 0296

(2014/02/16)

TOPICAL ANTIFUNGAL AGENT
An anti-fungal agent for tinea comprising as active ingredient a compound having the skeleton of 2-(1H-pyrazol-1-yl)phenol represented by the following formula (I) or (II) or a salt thereof is provided
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Paragraph 0482; 0483; 0484

(2013/12/04)

Double helix formation of oligoresorcinols in water: Thermodynamic and kinetic aspects
We previously reported that the oligoresorcinols formed double-stranded helices in neutral water through interstrand aromatic interactions. In the present study, we synthesized a new series of oligomers from the 2merto the 15mer to explore the thermodynamics, kinetics, and mechanism of the double helix formation of the oligoresorcinols in water. The double helix formation was dependent on the chain length of the oligomers and s ignificantly affected by solvent, pH, salt, and temperature. The free energy change (-?G) for the double helix formation linearly increased withthe chain length from the 4mer to the 11mer (ΔΔG = -0.94 kc al mol-1 unit-1), whereas it did not change for the oligomers longer than the 11 mer. The van't Hoff analysis of the 9mer revealed that the double helix formation was an enthalpically driven process (ΔH = -27 ± 1.5 kcal mol-1 and ΔS = -70 ± 5 cal mol-1 K-1), which was consistentwith the upfield shifts in the 1H NMR spectra and the hypoch romicity of the absorption spectra as a result of the interstrand aromatic interactions in water. Furthermore, the kinetic analysis of the chainexchange reaction between the double helices of the optically active an d optically inactive 11mers revealed a small ΔS?, suggesting that the chain exchange proceeds not via the dissociation-association pathway, but via the direct exchange pathway.
Goto, Hidetoshi,Furusho, Yoshio,Miwa, Kazuhiro,Yashima, Eiji
scheme or table
p. 4710 - 4719
(2009/09/26)

Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable 18F-labeled aryltrifluoroborates for use in PET imaging
(Chemical Equation Presented) Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(Ksolv) values correlate to a values with a ρ value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including 18F-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.
Ting, Richard,Harwig, Curtis W.,Lo, Justin,Li, Ying,Adam, Michael J.,Ruth, Thomas J.,Petrin, David M.
p. 4662 - 4670
(2008/09/20)

Oligoresorcinols fold into double helices in water
We report the first double helices with a controlled helicity in water based on oligoresorcinols as a new, simplest water-soluble structural motif. The molecular strands of the oligoresorcinols self-assemble into double helices with the aid of aromatic interactions in water as characterized by 1H NMR and absorption spectroscopies together with the X-ray crystallographic study of the pentamer. The double helix formation is sensitive to the chain length, solvent composition, and temperature. Moreover, a bias in the screw sense of the double helices was achieved by covalently attaching chiral substituents to both ends of the molecular strands. Copyright
Goto, Hidetoshi,Katagiri, Hiroshi,Furusho, Yoshio,Yashima, Eiji
p. 7176 - 7178
(2007/10/03)

C2-symmetric planar chiral ferrocene diamides by (-)-sparteine-mediated directed ortfto-lithiation. Synthesis and catalytic activity
(equation presented) A variety of highly enantioenriched singly and doubly (4) functionalized derivatives of 1,1′-N,N,N′,N′-tetraisopropylferrocenedicarboxamide 1 have been synthesized by (-)-sparteine (2)-mediated directed ortho-metalation and Pd-catalyz
Laufer, Radoslaw S.,Veith, Ulrich,Taylor, Nicholas J.,Snieckus, Victor
p. 629 - 631
(2007/10/03)