Month: October 2022

《General Asymmetric Synthetic Strategy for the α-Alkylated 2,5,6-Trisubstituted Pyran of Indanomycin and Related Natural Products》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Padma, Ravishetty; Srinivas, Beduru; Yadav, Jhillu S.; Mohapatra, Debendra K.. Application In Synthesis of 2-(Benzyloxy)acetaldehyde The article mentions the following:

A general synthetic strategy for convergent asym. synthesis of C1-C10 fragment I of tetraene-containing natural product indanomycin was achieved starting from 2-(benzyloxy)acetaldehyde which in turn was obtained from very inexpensive material cis-1,4-butene-diol. Key steps include Evans’ aldol reaction, HWE olefination, iodine-catalyzed tandem isomerization followed by C-O and C-C bond formation similar to our earlier report in constructing the trans-2,6-disubstituted dihydropyran ring and Evans’ asym. alkylation. In addition to this study using 2-(Benzyloxy)acetaldehyde, there are many other studies that have used 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Application In Synthesis of 2-(Benzyloxy)acetaldehyde) was used in this study.

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) may be used in the following syntheses: (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate ,(S)-5-benzyloxy-4-hydroxypentan-2-one, myxothiazols.Application In Synthesis of 2-(Benzyloxy)acetaldehyde

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Structural investigation of perfluorocarboxylic acid derivatives formed in the reaction with N,N-dimethylformamide dialkylacetals》 was written by Strozynska, Monika; Gross, Juergen H.; Schuhen, Katrin. Safety of N,N-Dimethylformamide Dimethyl Acetal And the article was included in European Journal of Mass Spectrometry in 2020. The article conveys some information:

A structural investigation of perfluorocarboxylic acid derivatives formed in the reaction with N,N-dimethylformamide dialkylacetals employing several techniques of mass spectrometry (MS) is described. Two derivatizing reagents, DMF di-Me acetal (DMF-DMA) and DMF diethylacetal (DMF-DEA) were used. In contrast to carboxylic acids, perfluorocarboxylic acids are not able to form alkyl esters as the main product in this reaction. We found that perfluorooctanoic acid (PFOA) forms a salt with N,N-dimethylformamide dialkylacetals. This salt undergoes a further reaction inside the injection block of a gas chromatograph (GC) by loss of CO2 and then forms 1,1-perfluorooctane-(N,N,N,N-tetramethyl)-diamine. The GC-MS experiments using both electron ionization (EI) and pos.-ion chem. ionization (PCI) revealed that the same reaction products are formed with either derivatizing reagent. Subjecting the perfluorocarboxylic acid derivative to electrospray ionization (ESI) and direct anal. in real time (DART), both pos.- and neg.-ion modes indicated that cluster ions are formed. In the pos.-ion mode, this cluster ion consists of two iminium cations and one PFOA anion, while in the neg.-ion mode, it comprises two PFOA anions and one cation. The salt structure was further confirmed by liquid injection field desorption/ionization (LIFDI) as well as IR spectroscopy. We propose a simple mechanism of N,N,N’,N’-tetramethylformamidinium cation formation. The structure elucidation is supported by specific fragment ions as obtained by GC-EI-MS and GC-PCI-MS anal.N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Safety of N,N-Dimethylformamide Dimethyl Acetal) was used in this study.

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Safety of N,N-Dimethylformamide Dimethyl Acetal

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Sagane, Fumihiro; Ogi, Kenta; Konno, Akinori; Kanamura, Kiyoshi published an article in 2021. The article was titled 《The effect of the coordination ability on the Mg plating/stripping behavior in Mg(N(CF3SO2)2)2/glyme based electrolytes》, and you may find the article in Journal of the Electrochemical Society.Application of 33100-27-5 The information in the text is summarized as follows:

The effect of the coordination ability of the solvent species on the Mg plating/stripping behavior was investigated. The Mg plating reaction in Mg(N(CF3SO2)2)2/diglyme was inhibited by the equimolar of 15-crown-5 ether (15C5) to Mg2+-ion. On the other hand, Mg plating took place in the solution by reducing the amount of 15C5 less than that of Mg2+-ion. FT-IR spectra showed that 15C5 preferentially solvated Mg2+-ion in the glyme based solutions The theor. calculation indicated the interaction between Mg2+-ion and each O atom in 15C5 was stronger than that with diglyme or larger sized crown ether. The results showed that the coordination ability of the solvent species could be the critical for the Mg plating reaction. The experimental process involved the reaction of 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Application of 33100-27-5)

1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Application of 33100-27-5

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2022,Mohammed, Ehtesham U. R.; Porter, Zoe J.; Jennings, Ian G.; Al-Rawi, Jasim M. A.; Thompson, Philip E.; Angove, Michael J. published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Synthesis and biological evaluation of 4H-benzo[e][1,3]oxazin-4-ones analogues of TGX-221 as inhibitors of PI3Kβ》.Quality Control of m-Methoxyphenol The author mentioned the following in the article:

A novel series of TGX-221 analogs was prepared that include isosteric replacement of the 4H-pyrido[1,2-a]pyrimidin-4-one with a 4H-benzo[e][1,3]oxazin-4-one I (R = Ph, 3,5-F2C6H3, 3-ClC6H4, etc.; X = O, NH) scaffold. The compounds that included an -CH(CH3)NH- type linker showed comparable activity to TGX-221 analogs with the isosterism supported by the comparative SAR anal. The analogs containing an -CH(CH3)O- linker were less active but still showed useful SAR including a favored o-Me substitution. The experimental part of the paper was very detailed, including the reaction process of m-Methoxyphenol(cas: 150-19-6Quality Control of m-Methoxyphenol)

m-Methoxyphenol(cas: 150-19-6) may be used in synthesis of:C(4) symmetric calix[4]resorcinarene, 2-nitroso-5-methoxyphenol, 6-methoxy-2(3H)-benzoxazoloneQuality Control of m-Methoxyphenol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 60656-87-3In 2021 ,《Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation》 appeared in Angewandte Chemie, International Edition. The author of the article were Shi, Chang-Yun; Eun, Jungmin; Newhouse, Timothy R.; Yin, Liang. The article conveys some information:

Catalytic asym. remote conjugate borylation is challenging as the control of regioselectivity is not trivial, the electrophilicity of remote sites is extenuated, and the remote asym. induction away from the carbonyl group is difficult. Herein, catalytic asym. conjugate 1,6-, 1,8- and 1,10-borylation was developed with excellent regioselectivity, which delivered α-chiral boronates in moderate to high yields with high enantioselectivity. The produced chiral boronate smoothly underwent oxidation, cross-coupling, and one-carbon homologation to give synthetically versatile chiral compounds in moderate yields with excellent stereoretention. Furthermore, a stereomechanistic anal. was conducted using DFT calculations, which provides insights into the origins of the regioselectivity. Finally, the present 1,6-borylation was successfully applied in an efficient one-pot asym. synthesis of (-)-7,8-dihydrokavain. In the experiment, the researchers used 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Related Products of 60656-87-3)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Related Products of 60656-87-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Adventitious root cultures of Decalepis salicifolia for the production of 2-hydroxy-4-methoxybenzaldehyde, a vanillin isomer flavor metabolite》 was written by Rodrigues, Vereena; Kumar, Amit; Prabhu, Kamasamudra N.; Pragadheesh, V. S.; Shukla, Ashutosh K.; Sundaresan, Velusamy. Computed Properties of C8H8O3This research focused onvanillin 2H4MB flavor production adventitious root culture Decalepis; 2-Hydroxy-4-methoxybenzaldehyde; Critically endangered; Endemic; Utleria salicifolia; Vanillin. The article conveys some information:

Decalepis salicifolia (Bedd. ex. Hook.f.) Venter is a potential natural source of the vanillin isomer, 2-hydroxy-4-methoxybenzaldehyde (2H4MB), an aromatic compound However, the utilization of the plant is hindered especially due to its critically endangered status and the root-specific accumulation of the compound The use of in vitro culture techniques offers a sustainable means for the production of valuable metabolites. In this study, an efficient system was established for the production of 2H4MB in the adventitious root cultures of D. salicifolia. Leaf explants of in vitro grown plants produced on an average 4.33 ± 2.07 number of roots with root initiation frequency of 95.69 ± 3.74% in woody plant medium supplemented with 0.5 mg/L α-naphthalene acetic acid (NAA) and 1.0 mg/L kinetin (Kn). The adventitious root biomass accumulation of 10.61 ± 0.89 g fresh weight (FW) was obtained in woody plant liquid media containing 0.5 mg/L NAA and 0.3 mg/L indole-3-butyric acid (IBA) in 60 days of inoculation. Field-grown plants of the same age produced 0.30 ± 0.02 g FW, which was 35-fold lower than the adventitious root culture. The total production of 2H4MB in the same growth period was 4.9-fold higher in adventitious root culture (139.54μg) as compared to field-grown plants (28.62μg). Furthermore, sucrose concentration of 2% was favorable for biomass accumulation, whereas 5% was favorable for 2H4MB production On the other hand, media pH 5.0 was suitable for biomass production and pH 7.0 was best suited for accumulation of 2H4MB. The adventitious roots also showed stable production of biomass and 2H4MB over 2 years. The established adventitious root culture system is suitable for further large-scale production of 2H4MB for flavor and fragrance industrial applications. Key points: • Biomass accumulation was higher in adventitious root cultures than in field-grown plants. • Manipulation of sucrose concentration and media pH led to increased 2H4MB production • Adventitious roots showed stable biomass and 2H4MB production over 2 years. In the experimental materials used by the author, we found 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Computed Properties of C8H8O3)

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is the main component of root bark essential oil of Periploca sepium Bunge. It is a potential tyrosinase inhibitor present in African medicinal plants. 2-Hydroxy-4-methoxybenzaldehyde was used in the synthesis of Schiff base ligand.Computed Properties of C8H8O3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《para-C-H Borylation of benzene derivatives by a bulky iridium catalyst》 was written by Saito, Yutaro; Segawa, Yasutomo; Itami, Kenichiro. SDS of cas: 214360-63-1 And the article was included in Journal of the American Chemical Society on April 22 ,2015. The article conveys some information:

A highly para-selective aromatic C-H borylation has been accomplished. By a new iridium catalyst bearing a bulky diphosphine ligand, Xyl-MeO-BIPHEP, the C-H borylation of monosubstituted benzenes can be affected with para-selectivity up to 91%. This catalytic system is quite different from the usual iridium catalysts that cannot distinguish meta- and para-C-H bonds of monosubstituted benzene derivatives, resulting in the preferred formation of meta-products. The para-selectivity increases with increasing bulkiness of the substituent on the arene, indicating that the regioselectivity of the present reaction is primarily controlled by steric repulsion between substrate and catalyst. Caramiphen, an anticholinergic drug used in the treatment of Parkinson’s disease, was converted into five derivatives via our para-selective borylation. The present [Ir(cod)OH]2/Xyl-MeO-BIPHEP catalyst represents a unique, sterically controlled, para-selective, aromatic C-H borylation system that should find use in streamlined, predictable chem. synthesis and in the rapid discovery and optimization of pharmaceuticals and materials. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1SDS of cas: 214360-63-1)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. SDS of cas: 214360-63-1 They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of C24H22N2O4On November 30, 2016 ,《Synthesis of new tetrazolyl derivatives of L- and D-phenylalanine》 appeared in Russian Journal of Organic Chemistry. The author of the article were Tolstyakov, V. V.; Tolstobrova, E. S.; Zarubina, O. S.; Popova, E. A.; Protas, A. V.; Chuprun, S. S.; Trifonov, R. E.. The article conveys some information:

(2S)- and (2R)-3-[4-(1H-Tetrazol-1-yl)phenyl]-2-aminopropionic acids were synthesized starting from L- and D-phenylalanine via azidation of Pr esters of (2S)- and (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-aminophenyl)propionic acids. The experimental process involved the reaction of Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2Synthetic Route of C24H22N2O4)

Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2) belongs to ethers.Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Synthetic Route of C24H22N2O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2013,Lercher, Lukas; McGouran, Joanna F.; Kessler, Benedikt M.; Schofield, Christopher J.; Davis, Benjamin G. published 《DNA Modification under Mild Conditions by Suzuki-Miyaura Cross-Coupling for the Generation of Functional Probes》.Angewandte Chemie, International Edition published the findings.Formula: C9H19NO4 The information in the text is summarized as follows:

We described an efficient method for the introduction of a variety of sensitive and useful functional groups by Suzuki-Miyaura cross-coupling to halogenated pyrimidine bases. After reading the article, we found that the author used tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6Formula: C9H19NO4)

tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6) belongs to ethers.Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Formula: C9H19NO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2014,Skouta, Rachid; Dixon, Scott J.; Wang, Jianlin; Dunn, Denise E.; Orman, Marina; Shimada, Kenichi; Rosenberg, Paul A.; Lo, Donald C.; Weinberg, Joel M.; Linkermann, Andreas; Stockwell, Brent R. published 《Ferrostatins Inhibit Oxidative Lipid Damage and Cell Death in Diverse Disease Models》.Journal of the American Chemical Society published the findings.SDS of cas: 139115-91-6 The information in the text is summarized as follows:

Ferrostatin-1 (Fer-1) inhibits ferroptosis, a form of regulated, oxidative, nonapoptotic cell death. We found that Fer-1 inhibited cell death in cellular models of Huntington’s disease (HD), periventricular leukomalacia (PVL), and kidney dysfunction; Fer-1 inhibited lipid peroxidation, but not mitochondrial reactive oxygen species formation or lysosomal membrane permeability. We developed a mechanistic model to explain the activity of Fer-1, which guided the development of ferrostatins with improved properties. These studies suggest numerous therapeutic uses for ferrostatins, and that lipid peroxidation mediates diverse disease phenotypes. In the experiment, the researchers used many compounds, for example, tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6SDS of cas: 139115-91-6)

tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.SDS of cas: 139115-91-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem