Category: 1860-58-8

Schrittwieser, Joerg H. published the artcileBiocatalytic Enantioselective Oxidative C-C Coupling by Aerobic C-H Activation, Application In Synthesis of 1860-58-8, the publication is Angewandte Chemie, International Edition (2011), 50(5), 1068-1071, S1068/1-S1068/144, database is CAplus and MEDLINE.

The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C-C coupling that leads to a new intramol. bond. This unique transformation requires O₂ as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloid derivatives by kinetic resolution

Angewandte Chemie, International Edition published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Application In Synthesis of 1860-58-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Schrittwieser, Joerg H. published the artcileBiocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids, COA of Formula: C15H14O3, the publication is Journal of Organic Chemistry (2011), 76(16), 6703-6714, database is CAplus and MEDLINE.

A chemoenzymic approach for the asym. total synthesis of the title compounds was described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asym. key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine (I), a sedative and muscle relaxing agent. The racemic substrates required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-C¦Á alkylation approach. The chemoenzymic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline (II), and gave overall yields of up to 20% over 5-9 linear steps.

Journal of Organic Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, COA of Formula: C15H14O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

DeBerardinis, Albert M. published the artcileVitamin D3 analogues that contain modified A- and seco-B-rings as hedgehog pathway inhibitors, Product Details of C15H14O3, the publication is European Journal of Medicinal Chemistry (2015), 156-171, database is CAplus and MEDLINE.

The hedgehog (Hh) signaling pathway is a developmental signaling pathway that has been implicated as a target for anti-cancer drug development in a variety of human malignancies. Several natural and synthetic vitamin D-based seco-steroids have been identified as potent inhibitors of Hh signaling with chemotherapeutic potential. These include the previously characterized analog 4, which contains the northern CD-ring/side chain region of vitamin D3 (VD3) linked to an aromatic A-ring mimic through an ester bond. To further explore structure-activity relationships for this class of VD3-based Hh pathway inhibitors, we have designed, synthesized and evaluated several series of compounds that modify the length, composition, and stereochem. orientation of the ester linker. These studies have identified compounds 54 and 55, which contain an amine linker and an aromatic A-ring incorporating a para-phenol, as new lead compounds with enhanced potency against the Hh pathway (IC₅₀ values = 0.40 and 0.32 ¦ÌM, resp.).

European Journal of Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Product Details of C15H14O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Faller, J. W. published the artcileA new solvatochromic chelating agent, Quality Control of 1860-58-8, the publication is Analytica Chimica Acta (1965), 32(6), 586-9, database is CAplus.

cf. CA 59, 10744h; 62, 6597e. The preparations are described of a solvatochromic chelating agent, 2 – (4′-hydroxy-3′-methoxystyryl)-5-(8-hydroxy-5-quinaldylmethyl)-1-methyl-8-hydroxyquinolinium Cl (1 merocyanine) (I); I.H₂O m. 250¡ã (decomposition), by the piperidine catalyzed condensation of the N-Me derivative of bis(8-hydroxy-5-quinaldyl)methane with vanillin; and of a bifunctional chelating agent 5-(8-hydroxy-5-quinolylmethyl)-8-hydroxyquinaldine (II) (m. 219-20¡ã), following the methods of Fiedler (CA 57, 7227h) for similar compounds The effect of solvent polarity on the absorption spectra of I is shown. The principal maximum and the log ¦Å (molar absorptivities) of the following I solutions are: 0.1NHCl 325,414; 4.20, 4.46; 0.01N KOH 375, 478; 4.15, 4.50; 90% MeOH- 0.01N KOH 392, 514; 4.09, 4.57; 90% PrOH-, 397, 525; 4.13, 4.58; 90% iso-PrOH-, 400, 526; 4.15, 4.59; 90% Me₂CO-0.01N KOH 405, 530; 4.40, 4.66; PhCH₂OH (saturated with 0.01N KOH) 385, 545; 4.32, 4.06; CHCl₃ (saturated with 0.01N KOH) 389, 611; 4.74, 3.52; 30% C₅H₅N (III) -, 509; 4.58; 50% III -, 399, 527; 4.14, 4.57; 80% III-, 401, 530, 561; 4.38, 4.23, 4.23; 86% III-, 593; 3.95; 94% III-, 403, 605; 4.57, 3.91; and 98% III-0.01N KOH solvent, 609 m¦Ì; 3.89, resp. At low III concentrations, protons were removed only from the O atoms of the vanillylidene and 8-hydroxyquinaldyl groups, while at the higher (¡Ý80%) III concentrations the proton was also removed from the remaining OH. At pH 9, I formed red H₂O-insoluble, PhCH₂OH soluble chelates with Ni²⁺, Cu²⁺, Zn²⁺, Co²⁺, Mg²⁺, Al³⁺ and Fe³⁺; at pH 5, I gave orange compounds with Ni²⁺, Cu²⁺, Zn²⁺, and Co²⁺, with solubility similar to that of the red chelates. The PhCH₂OH/alk. aqueous I solubility ratio is ?60. The stoichiometric Cu-II₂ (containing 9.2% Cu) and Al-II₃ (containing 2.8% Al) were prepared as described by Hollingshead (Oxine and its Derivatives, London: Butterworths, 1954). The ir spectra of II, on KBr pellets, had OH and aromatic bands and strong maximum at 12.1, 12.8 and 14.1 ¦Ì. The principal uv maximum of II, and the resp. log ¦Å were: (in 0.1N HCl) 258, 4.94; 313, 3.62; 324, 3.61; and 371, 3.70; (in 0.1N NaOH) 258, 4.74; 344, 3.84; and 365 m¦Ì, 3.82.

Analytica Chimica Acta published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Quality Control of 1860-58-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Pearson, Anthony J. published the artcileModel studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry, Safety of 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Journal of Organic Chemistry (1992), 57(6), 1744-52, database is CAplus.

Preparation of several protected L–p-chlorophylalanine derivatives in high optical purity and their complex formation with [CpRu(MeCN)₃]PF₆ (Cp = cyclopentadienyl) are described. The complexation reaction, as well as subsequent photochem. decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogs using a number of known coupling reagents were unsuccessful.

Journal of Organic Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Safety of 2-(3-(Benzyloxy)phenyl)acetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Suguna, H. published the artcilePhotolytic syntheses of dl-anolobine and dl-9-hydroxy-2,3-methylenedioxyberbine, Quality Control of 1860-58-8, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1977), 15B(5), 416-18, database is CAplus.

Debenzylation of the isoquinoline I (R = PhCH2, R1 = Br) gave I (R = H, R1 = Br) and bromohydroxymethylenedioxyberbine II. Photolysis of I (R = H, R1 = Br).HCl gave (¡À)-anolobine (III), I (R = R1 = H), and II. II on reductive debromination gave 9-hydroxy-2,3-methylenedioxyberbine. IR spectrum of synthetic anolobine was identical with that of natural anolobine.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C21H37BO, Quality Control of 1860-58-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Xiao, Zhu-Ping published the artcile4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation, Synthetic Route of 1860-58-8, the publication is Bioorganic & Medicinal Chemistry (2011), 19(13), 3884-3891, database is CAplus and MEDLINE.

A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-pos. organisms, and 27 is the most potent agent against Staphylococcus aureus ATCC 25923 with MIC₅₀ value of 0.23 ¦Ìg/mL.

Bioorganic & Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C19H15NO3, Synthetic Route of 1860-58-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Arasappan, Ashok published the artcileP2-P4 Macrocyclic inhibitors of hepatitis C virus NS3-4A serine protease, Synthetic Route of 1860-58-8, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(15), 3960-3965, database is CAplus and MEDLINE.

Synthesis and HCV NS3 serine protease inhibitory activity of 4-hydroxyproline derived macrocyclic inhibitors and SAR around this macrocyclic core is described in this communication. X-ray structure of inhibitor I bound to the protease is discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Synthetic Route of 1860-58-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tomita, Masao published the artcileSyntheses of biscoclaurine alkaloids. III. Synthesis of dl-3,4′-bis(2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolylmethyl)diphenyl ether, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Yakugaku Zasshi (1959), 1019-22, database is CAplus.

cf. C.A. 53, 5315a. Vanillin was methylated with alk. Me₂SO₄ to veratraldehyde, which was condensed with MeNO₂ in MeOH and MeNH₂ to give 3,4-(MeO)₂C₆H₃CH:CHNO₂, which was electrolytically reduced in 15:12:45 AcOH-HCl-MeOH to 3,4-(MeO)₂C₆H₃CH₂CH₂NH₂ (I); oxalate m. 178¡ã. 3-PhCH₂OC₆H₄ CH₂CO₂H (II), m. 124-6¡ã, was prepared through the route of 3-O₂NC₆H₄CHO, m. 56-8¡ã, 3-HOC₆H₄CHO, m. 103-4¡ã, 2-phenyl-4-(3-benzyloxybenzylidene)-2-oxazolin-5-one, m. 129-31¡ã, to II. I (from 5.5 g. of its oxalate) in Et₂O and 50 ml. 10% KOH treated dropwise with 3-PhCH₂OC₆H₄CH₂COCl (from 5 g. II in CHCl₃ and SOCl₂), stirred 1 hr., the Et₂O layer and CHCl₃ extract of the aqueous layer concentrated, washed with dilute HCl and H₂O and the product recrystallized (MeOH) gave 6 g. 3-PhCH₂OC₆H₄CH₂CONHCH₂CH₂C₆H₃(OMe)₂-3,4 (III), needles, m. 97-100¡ã. III (3 g.) in 45 ml. PhMe and 6 ml. POCl₃ refluxed 1.5 hrs., and the product treated as usual gave 2.8 g. 1-(3-benzyloxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-HCl (IV), prisms, m. 203-5¡ã (decomposition); the free base, needles, m. 84-6¡ã; picrate, columns, m. 207-9¡ã (MeOH). The free base (from 250 mg. IV) in MeOH and 1 ml. MeI refluxed 2 hrs., the product concentrated, the residue in MeOH at 0¡ã treated dropwise with 500 mg. NaBH₄ in MeOH, heated 1 hr. at 50¡ã, the solution concentrated, the residue in H₂O made alk. and extracted with Et₂O gave 1-(3-benzyloxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (V), oil, which yielded 220 g. picrate, columns, m. 164-5¡ã (decomposition). V (870 mg.) in 40 ml. 20% HCl refluxed 30 min., the product washed with Et₂O, made alk. with NaHCO₃, extracted with CHCl₃, stirred with 10% NaOH, the NaOH layer treated with NH₄Cl and NH₄OH, and extracted with CHCl₃ yielded 57% 1-(3-HOC₆H₄CH₂) analog (VI) of V, columns, m. 136-7.5¡ã; picrate, columns, m. 180-3¡ã (decomposition). VI (100 mg.) in MeOH and CH₂N₂ (from 1 g. nitrosomethylurea) in Et₂O kept 2 days at room temperature, the solution concentrated, the residue in dilute HCl made alk. with NaOH and the product extracted with Et₂O gave 80 mg. 1-(3-MeOC₆H₄CH₂) analog (VII) of V, oil; VII.HCl.0.5H₂O, needles, m. 198-201¡ã; VII.HI, needles, m. 227-30¡ã (decomposition). K (60 mg.) in 6 ml. MeOH heated with 450 mg. dl-VI and the MeOH removed gave the K salt of dl-VI, which treated with dl-1-(4-bromobenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (from 1050 mg. of its picrate, m. 183-3.5¡ã) in Et₂O, the Et₂O removed, the residue with 75 mg. Cu and 60 mg. Cu(OAc)₂ heated 30 min. at 180-5¡ã, 25 min. at 185-95¡ã, and 10 min. at 105-200¡ã, cooled, the product extracted with Et₂O, the phenolic base removed by washing with 2% KOH, and the nonphenolic base refined by chromatographic method yielded 160 mg. dl-3,4′-bis(2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolylmethyl)diphenyl ether (VIII), oil; VIII.2(CO₂H)₂.H₂O, needles, m. 185-8¡ã (decomposition) (MeOH-Me₂CO); styphnate, VIII.2(C₆H₃O₈N₃), prisms, m. 143-6¡ã (decomposition) (Me₂CO-EtOH).

Yakugaku Zasshi published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C9H8BNO2, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Srivastava, Apurva K. published the artcileStudies in development of immunoassays: Part I. Synthesis of 3,4-trans-2,2-dimethyl-3-(m-hydroxyphenyl)-4-[p-(pyrrolidinoethoxy)phenyl]-7-methoxychroman-BSA conjugate, an immunogen of centchroman, Application of 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1994), 33B(7), 671-3, database is CAplus.

The synthesis of 3,4-trans-2,2-dimethyl-3-(m-hydroxyphenyl)-4-[p-(pyrrolidinoethoxy)phenyl]-7-methoxychroman-bovine serum albumin (BSA) conjugate I, an immunogen for antibody production against centchroman, has been carried out. Thus, diphenylcoumarin II was methylated, alkylated with ¦Â-pyrrolidinoethyl chloride, hydrogenated, and isomerized to give I.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C8H19NO2, Application of 2-(3-(Benzyloxy)phenyl)acetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia