Month: December 2022

Xie, Jianing published the artcilePd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl ¦Ã-lactones: access to caprolactam diversity, Synthetic Route of 2051-95-8, the publication is Chemical Science (2020), 11(33), 8839-8845, database is CAplus and MEDLINE.

A stereoselective amination/cyclization cascade process was developed that allowed for the preparation of a series of unsaturated and substituted caprolactam derivatives I [R = Ph, 3,5-di-MeC₆H₃, 2-naphthyl, etc.; R¹ = Ph, Bn, CH(Ph)₂, etc.; R² = H, Me, R³ = CH₂, C=CH₂, CHPh] in good yields. This conceptually novel protocol took advantage of the easy access and modular character of vinyl ¦Ã-lactones that could be prepared from simple precursors. Activation of the lactone substrate in the presence of a suitable Pd precursor and newly developed phosphoramidite ligand offers a stereocontrolled ring-opening/allylic amination manifold under ambient conditions. The intermediate (E)-configured ¦Å-amino acid could be cyclized using a suitable dehydrating agent in an efficient one-pot, two-step sequence. This overall highly chemo-, stereo- and regio-selective transformation streamlined the production of a wide variety of modifiable and valuable caprolactam building blocks in an operationally attractive way.

Chemical Science published new progress about 2051-95-8. 2051-95-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ketone, name is 3-Benzoylpropionicacid, and the molecular formula is C9H5ClO4S, Synthetic Route of 2051-95-8.

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

Xie, Jianing published the artcilePd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl ¦Ã-lactones: access to caprolactam diversity, Formula: C11H10O3, the publication is Chemical Science (2020), 11(33), 8839-8845, database is CAplus and MEDLINE.

A stereoselective amination/cyclization cascade process was developed that allowed for the preparation of a series of unsaturated and substituted caprolactam derivatives I [R = Ph, 3,5-di-MeC₆H₃, 2-naphthyl, etc.; R¹ = Ph, Bn, CH(Ph)₂, etc.; R² = H, Me, R³ = CH₂, C=CH₂, CHPh] in good yields. This conceptually novel protocol took advantage of the easy access and modular character of vinyl ¦Ã-lactones that could be prepared from simple precursors. Activation of the lactone substrate in the presence of a suitable Pd precursor and newly developed phosphoramidite ligand offers a stereocontrolled ring-opening/allylic amination manifold under ambient conditions. The intermediate (E)-configured ¦Å-amino acid could be cyclized using a suitable dehydrating agent in an efficient one-pot, two-step sequence. This overall highly chemo-, stereo- and regio-selective transformation streamlined the production of a wide variety of modifiable and valuable caprolactam building blocks in an operationally attractive way.

Chemical Science published new progress about 15732-75-9. 15732-75-9 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ketone, name is 2-Methylene-4-oxo-4-phenylbutanoic acid, and the molecular formula is C9H5ClO4S, Formula: C11H10O3.

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

Wang, Ping published the artcileEncouraging progress in the ¦Ø-aspartylation of complex oligosaccharides as a general route to ¦Â-N-linked glycopolypeptides, Formula: C9H12O3S, the publication is Journal of the American Chemical Society (2011), 133(5), 1597-1602, database is CAplus and MEDLINE.

Described herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The ¦Ø-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the ¦Ø-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochem. defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed.

Journal of the American Chemical Society published new progress about 77189-99-2. 77189-99-2 belongs to catalysis-chemistry, auxiliary class Thiophenol,Benzene,Ether, name is 2,4,6-Trimethoxybenzenethiol, and the molecular formula is C9H8O4, Formula: C9H12O3S.

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

Lu, Guo-qing published the artcileDesign, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs, Name: (E)-3-(3-Nitrophenyl)acrylic acid, the publication is European Journal of Medicinal Chemistry (2019), 282-296, database is CAplus and MEDLINE.

Aryltriazolylphenylaminosulfonyl uracils such as I (R = Ph, 2-MeC₆H₄, 3-MeC₆H₄, 4-MeC₆H₄, 2-FC₆H₄, 3-FC₆H₄, 4-FC₆H₄, 2-ClC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄) were prepared as thymidylate synthase inhibitors for potential use as antitumor agents. The aryltriazolylphenylaminosulfonyl uracils were tested for their inhibition of human cancer cell lines and for their toxicities in normal human cell lines; selected compounds were tested for their inhibition of human thymidylate synthase (hTS). I (R = 4-ClC₆H₄) was the most effective antitumor agent of the compounds tested, inhibiting the growth of A549 cells with an IC₅₀ value of 1.18 ¦ÌM and inhibiting hTS with an IC₅₀ value of 0.13 ¦ÌM, superior to comparable data for the known antitumor agent pemetrexed. I (R = 4-ClC₆H₄) inhibited cell cycle advancement in G1/S phase and induced apoptosis. I (R = 4-ClC₆H₄) likely down-regulates the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit cell cycle progression, and induced intrinsic apoptosis by activating caspase-3 and reducing the ratio of bcl-2 to bax.

European Journal of Medicinal Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Name: (E)-3-(3-Nitrophenyl)acrylic acid.

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

Zhang, Jun published the artcileSynthesis of m-aminophenyl acetylene, Name: (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Zhongguo Yiyao Gongye Zazhi (2012), 43(10), 812-814, database is CAplus.

M-Aminophenyl acetylene, the key intermediate of antitumor agent erlotinib hydrochloride, was synthesized from m-nitrobenzaldehyde by Perkin reaction, bromine addition, elimination of hydrogen bromide and decarboxylation to give (Z)-1-bromo-2-(3-nitrophenyl)ethylene, followed by reaction with NaH and reduction with Fe/HCl. The overall yield was about 45%.

Zhongguo Yiyao Gongye Zazhi published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H9BrO2, Name: (E)-3-(3-Nitrophenyl)acrylic acid.

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

Zhang, Jianfeng published the artcilePreparation and acidic dissociation constants determination of phenylenedioxybis(acetic acid), Product Details of C10H10O6, the publication is Huaxue Shijie (2002), 43(3), 135-137, database is CAplus.

Three types of phenylenedioxybis(acetic acid) were prepared by reacting dihydroxybenzene with chloroacetic acid in an alkali solution Controlling the pH value of the reaction system and applying a new self-sealing apparatus, high yield and selectivity were obtained. The acid dissociation constants of the samples were obtained for the first time by elec. potential titration A regression method was adopted in the data processing, which made the results more precise and reliable. CNDO/2 quantum chem. calculation method was used to explain the results of acid dissociation constant measurements.

Huaxue Shijie published new progress about 5411-14-3. 5411-14-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2,2-(1,2-Phenylenebis(oxy))diacetic acid, and the molecular formula is C7H10O4, Product Details of C10H10O6.

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

Song, Liping published the artcileFluorine-containing furan derivatives from the Michael addition of ethyl 4,4,4-trifluoro-3-oxobutanoate with ¦Â-nitrostyrenes, Product Details of C10H11NO4, the publication is Synlett (2010), 830-834, database is CAplus.

Et 4,4,4-trifluoro-3-oxobutanoate reacted with nitrostyrenes in the presence of Et₃N to afford Et 5-(hydroxyimino)-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates along with a small amount of Et 2-hydroxy-5-imino-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates, e.g., I. Treatment of Et 5-(hydroxyimino)-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates with 1.2 equiv of TsOH in t-BuOH, afforded Et 2-hydroxy-5-imino-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates in good yields. However, Et 2-ethoxy or 2-methoxy-5-oxo-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates were obtained as major products in EtOH or MeOH along with a small amount of Et 2-hydroxy-5-imino-4-aryl-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylates.

Synlett published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C14H31NO2, Product Details of C10H11NO4.

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

Heydari, Paniz published the artcileDevelopment and validation of an LC-MS/MS assay for the quantification of cintirorgon (LYC-55716) in mouse plasma and tissue homogenates, Quality Control of 2055536-64-4, the publication is Journal of Pharmaceutical and Biomedical Analysis (2022), 114421, database is CAplus and MEDLINE.

Cintirorgon (LYC-55716) is a promising first-in-class antitumor agent as a ROR¦Ã agonist in the treatment against various types of cancer. To support preclin. mouse studies, a bioanal. method was developed and successfully applied for quantification of cintirorgon in mouse plasma and tissue homogenates using LC-MS/MS. The method was fully validated in mouse plasma and partial validation was performed in eight different homogenates originating from brain, kidney, liver, lung, small intestine, small intestine content, spleen, and testis. Sample preparation was performed using 96-well plates for fast and efficient anal. Protein precipitation was done by addition of 20¦ÌL acetonitrile containing monensin as internal standard to 10¦ÌL sample. Chromatog. separation was achieved on a Polaris 3 C18-A column using gradient elution with 0.2% (volume/volume) formic acid and 0.2% (volume/volume) ammonium hydroxide in water (A) and methanol (B) as eluents. The total run time was 3 min. Detection was carried out with a triple quadrupole mass spectrometer with electrospray ionization operated in the pos. ion-mode. Quantification could be accomplished within a linear validated concentration range of 5-4,000 ng/mL (10-4,000 ng/mL in brain homogenates) with an intra- and inter-day precision between 4.6-14.7% and 5.1-15.6% (including the LLOQ), resp., and accuracies between 89.1%-111.2%. The method was successfully applied to a preclin. study with cintirorgon in mice.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 2055536-64-4. 2055536-64-4 belongs to catalysis-chemistry, auxiliary class Metabolic Enzyme,ROR, name is (S)-3-(6-(3-(Difluoromethoxy)-5-fluorophenyl)-4-((3-(trifluoromethyl)phenyl)sulfonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-2,2-dimethylpropanoic acid, and the molecular formula is C27H23F6NO6S, Quality Control of 2055536-64-4.

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

Song, Lijuan published the artcileNatural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO₃ for synthesis of disulfanes in water, SDS of cas: 119-80-2, the publication is Green Chemistry (2019), 21(6), 1432-1438, database is CAplus.

To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes RSSR¹ [R = 4-MeC₆H₄, cyclohexyl, 2-thienyl, etc.; R¹ = t-Bu, 4-ClC₆H₄, 4-H₂NC₆H₄, etc.], using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO₃ as a cocatalyst, O₂ as the terminal oxidant and water as the solvent, was successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various sym. and unsym. disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrated the practicability of our method.

Green Chemistry published new progress about 119-80-2. 119-80-2 belongs to catalysis-chemistry, auxiliary class sulfides,Carboxylic acid,Benzene, name is 2,2′-Dithiodibenzoic acid, and the molecular formula is C14H31NO2, SDS of cas: 119-80-2.

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

Li, Jiu-ling published the artcilePalladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C₁-benzoyl isoquinolines from isoquinoline N-oxides and nitroalkenes, Computed Properties of 4230-93-7, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(65), 10028-10031, database is CAplus and MEDLINE.

C₁-Benzoyl isoquinolines I [R = H, CH₃; R¹ = 6-CH₃, 5-Cl, 5-NO₂, etc.; R² = 4-H₃COC₆H₄, 4-(CH₃)₂CHC₆H₄, naphthalen-2-yl, etc.] can be generated via a palladium(II)-catalyzed C-C and C-O coupling of isoquinoline N-oxides II with aromatic nitroalkenes R²C=CHNO₂. The reaction proceeds through remote C-H bond activation and subsequent intramol. oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.

Chemical Communications (Cambridge, United Kingdom) published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Computed Properties of 4230-93-7.

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