Month: November 2022

The author of 《Highly Efficient and Robust Enantioselective Liquid-Liquid Extraction of 1,2-Amino Alcohols utilizing VAPOL- and VANOL-based Phosphoric Acid Hosts》 were Pinxterhuis, Erik B.; Gualtierotti, Jean-Baptiste; Wezenberg, Sander J.; de Vries, Johannes G.; Feringa, Ben L.. And the article was published in ChemSusChem in 2018. Synthetic Route of C9H13NO The author mentioned the following in the article:

The large-scale production of enantiopure compounds in a cost-effective and environmentally friendly manner remains one of the major challenges of modern-day chem. The resolution of racemates through enantioselective liquid-liquid extraction was developed as a suitable solution but has remained largely underused, owing to a lack of highly efficient and robust chiral hosts to mediate the process. This paucity of hosts can in part be attributed to a poor understanding of the underlying principles behind these processes hindering the design of more efficient selectors. A previously untested class of hosts, VAPOL and VANOL derived phosphoric acids, was studied in depth for the efficient enantioselective liquid-liquid extraction of 1,2-amino alcs. A systematic investigation of extraction parameters was conducted, revealing many key interactions and DFT calculations illustrate the binding modes for the 1:1 complexes that are involved in chiral recognition. The resulting, now-optimized, procedures are highly robust and easy to implement. They are also easily scalable, as demonstrated by U-tube experiments In the experiment, the researchers used 2-Amino-2-(4-methylphenyl)ethan-1-ol(cas: 157142-48-8Synthetic Route of C9H13NO)

2-Amino-2-(4-methylphenyl)ethan-1-ol(cas: 157142-48-8) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Synthetic Route of C9H13NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Chemical Science included an article by Stateman, Leah M.; Wappes, Ethan A.; Nakafuku, Kohki M.; Edwards, Kara M.; Nagib, David A.. HPLC of Formula: 13325-10-5. The article was titled 《Catalytic β C-H amination via an imidate radical relay》. The information in the text is summarized as follows:

The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcs. e.g., 4-trichloroacetamidyl cholesterol by an imidate-mediated radical relay. In contrast to the first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes (6-methyl-5-hepten-2-one, 3,7-dimethyl-2,6-octadienol), alkynes (isonicotinonitrile), alcs.(1-octanol), carbonyls (Me 2-(([(4-nitrobenzene)sulfonyl]oxy)amino)-3-phenylpropanoate) and heteroarenes (quinoline, benzofuran, benzo[b]thiophene, etc.). Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity. In the part of experimental materials, we found many familiar compounds, such as 4-Aminobutan-1-ol(cas: 13325-10-5HPLC of Formula: 13325-10-5)

4-Aminobutan-1-ol(cas: 13325-10-5) is used in the synthesis of NSAIDs with anti-inflammatory properties. Also used in the synthesis of polyamine transport ligands with specificity against human cancers allowing easy access to specific cancer cells.HPLC of Formula: 13325-10-5

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Green Chemistry included an article by Chakrabarti, Kaushik; Maji, Milan; Kundu, Sabuj. Application In Synthesis of 3-Pyridinemethanol. The article was titled 《Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water》. The information in the text is summarized as follows:

An efficient methodol. for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcs. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies. After reading the article, we found that the author used 3-Pyridinemethanol(cas: 100-55-0Application In Synthesis of 3-Pyridinemethanol)

3-Pyridinemethanol(cas: 100-55-0) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Application In Synthesis of 3-Pyridinemethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Science China: Chemistry included an article by Li, Xiaonan; Chen, Pinhong; Liu, Guosheng. Formula: C6H12O. The article was titled 《Iodine(III) reagent (ABX-N3)-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes》. The information in the text is summarized as follows:

Anti-Markovnikov hydroazidation of unactivated alkenes using ABX-N3 as an initiator has been developed at room temperature, wherein hydrogen azide (HN3) acts as both hydrogen source and azidation agent. Notably, the HN3 reagent was generated from azidotrimethylsilane (TMSN3) and acetic acid in situ. The reaction itself displays broad substrate scope, good yields, and excellent regioselectivities. In the experiment, the researchers used 5-Hexen-1-ol(cas: 821-41-0Formula: C6H12O)

5-Hexen-1-ol(cas: 821-41-0) is a volatile organic compound. Further, it is used to prepare 6-bromo-hex-1-ene by reaction with phosphorus tribromide.Formula: C6H12O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Tetrahedron Letters included an article by Qiu, Zhenjiang; Zhu, Mingxiang; Zheng, Lu; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng. HPLC of Formula: 18621-18-6. The article was titled 《Regioselective α-benzylation of 3-iodoazetidines via Suzuki cross-coupling》. The information in the text is summarized as follows:

An efficient protocol for the synthesis of α-benzyl azetidines I [R = 4-F3COC6H4, 2-F-C6H4, naphthalen-2-yl, etc.; R1 = C(O)OCH2C6H5, C(O)OC(CH3)3] starting from benzylboronic acid pinacol ester derivatives II and 3-iodoazetidine III was developed. A wide range of α-benzyl azetidine derivatives I was obtained in moderate to good yields with high regioselectivity (>99%). In the experimental materials used by the author, we found Azetidin-3-ol hydrochloride(cas: 18621-18-6HPLC of Formula: 18621-18-6)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.HPLC of Formula: 18621-18-6 Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Bioorganic Chemistry included an article by Choi, Wonbeen; Villegas, Valente; Istre, Hannah; Heppler, Ben; Gonzalez, Niki; Brusman, Nicole; Snider, Lindsey; Hogle, Emily; Tucker, Janelle; Onate, Alma; Onate, Sandra; Ma, Lili; Paula, Stefan. HPLC of Formula: 26153-38-8. The article was titled 《Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties》. The information in the text is summarized as follows:

Inhibitors of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ROS in the aftermath of a heart attack or stroke. To combine these two properties in a single mol., we synthesized and characterized the non-purine XO inhibitor caffeic acid phenethylester (CAPE) and 19 derivatives using a convenient microwave-assisted Knoevenagel condensation protocol. Varying systematically the number and positions of the hydroxyl groups at the two Ph rings, we derived structure-activity relationships based on exptl. determined XO inhibition data. Mol. docking suggested that critical enzyme/inhibitor interactions involved π-π interactions between the phenolic inhibitor ring and Tyr914, hydrogen bonds between inhibitor hydroxyl groups and Glu802, and hydrophobic interactions between the CAPE Ph ring and non-polar residues located at the entrance of the binding site. To effectively scavenge the stable radical DPPH, two hydroxyl groups in 1,2- or 1,4-position at the Ph ring were required. Among all compounds tested, E-Ph 3-(3,4-dihydroxyphenyl)acrylate, a CAPE analog without the Et tether, showed the most promising properties. In the experimental materials used by the author, we found 3,5-Dihydroxybenzaldehyde(cas: 26153-38-8HPLC of Formula: 26153-38-8)

3,5-Dihydroxybenzaldehyde(cas: 26153-38-8) is used as a building block in the synthesis of more complex structures. It is also used in the synthesis of terbutaline, which is an important bronchodilator.HPLC of Formula: 26153-38-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Inorganica Chimica Acta included an article by Elmas, Gamze; Okumus, Aytug; Hokelek, Tuncer; Kilic, Zeynel. Related Products of 156-87-6. The article was titled 《Phosphorus-nitrogen compounds. Part 52. The reactions of octachlorocyclotetraphosphazene with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide: Investigations of spectroscopic, crystallographic and stereogenic properties》. The information in the text is summarized as follows:

The reaction of octachlorocyclotetraphosphazene (tetramer, N4P4Cl8, 1) with two mole equivalent of Na 3-(N-ferrocenylmethylamino)-1-propanoxide (2) gave the novel ansa-spiro (3), 2-trans-6-dispiro (4), 2-cis-6-dispiro (5), 2-trans-4-dispiro (6) and 2-cis-4-dispiro (7) cyclotetraphosphazenes. However, when the reaction was carried out with 1 and three mole equivalent of 2, seven products observed with respect to the 31P NMR spectrum of the reaction mixture Five of these products were identified as 3, 4, 5, 6 and 7, and the other two products are expected to be 2-trans-4-trans-6-trispiro (8) derived from 4 and/or 6, and 2-trans-4-cis-6-trispiro (9) derived from 5 and/or 7. Both of the trispiro products (8 and 9) were not isolated using column chromatog. Besides, when the reaction was made with 1 and excess amount of 2, the tetraspiro products were not observed by TLC and 31P NMR spectrum of the reaction mixture The structures of cyclotetraphosphazene derivatives were verified by ESI-MS, FTIR, 1H, 13C and 31P NMR spectral data. The mol. and solid state structures of 3, 5 and 6 were established by x-ray diffraction method. The x-ray crystallog. data indicate that compounds 3 and 6 have three-different and two equivalent chiral P centers, resp. The absolute configurations of 3 and 6 also are as SS’S” and RR. After reading the article, we found that the author used 3-Aminopropan-1-ol(cas: 156-87-6Related Products of 156-87-6)

3-Aminopropan-1-ol(cas: 156-87-6) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Related Products of 156-87-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Chemistry of Materials included an article by Das, Gobinda; Nagaraja, Sharadhi; Sridurai, Vimala; Shinde, Digambar B.; Addicoat, Matthew; Prakasam, Thirumurugan; Gandara, Felipe; Ravaux, Florent; Sharma, Sudhir Kumar; Nair, Geetha G.; Lai, Zhiping; Jagannathan, Ramesh; Olson, Mark A.; Trabolsi, Ali. Application In Synthesis of 2,6-Pyridinedimethanol. The article was titled 《Redox-Triggered Buoyancy and Size Modulation of a Dynamic Covalent Gel》. The information in the text is summarized as follows:

The development of stimuli-responsive materials capable of transducing external stimuli into mech. and phys. changes has always been an intriguing challenge and an inspiration for scientists. Several stimuli-responsive gels have been developed and applied to biomimetic actuators or artificial muscles. Redox-active actuators in which the mech. motion is driven chem. or electrochem. have attracted much interest, and their actuation mechanism is based on the change in electrostatic repulsion and the loss or gain of counterions to balance newly formed charges. Actuation can also be promoted by changing the hydration state of the material, leading to the release/adsorption of water mols. from the network, inducing a direct shrinking/swelling of the material, resp. A cationic crystalline dynamic covalent gel was obtained via the formation of imine bonds between 2,6-diformyl pyridine and triamino guanidinium chloride. The gel exhibits a reversible contraction/expansion behavior in response to base (oxidation, -H+, -e-) and acid (reduction +H+, +e-), resp. The oxidation induces a color change and contraction of the gel with a concomitant increase in its strength. As synthesized, the cationic gel is denser than water and sinks when placed in water. Upon oxidation, the radical cationic gel expels water mols., rendering it less dense than water and the gel is propelled to the surface without any loss of its structural integrity. These results demonstrate that a careful choice of amine and aldehyde linkers can give rise to imine-linked materials capable of tolerating and resisting extreme acidic and basic conditions while performing work. In the experiment, the researchers used many compounds, for example, 2,6-Pyridinedimethanol(cas: 1195-59-1Application In Synthesis of 2,6-Pyridinedimethanol)

2,6-Pyridinedimethanol(cas: 1195-59-1) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Application In Synthesis of 2,6-Pyridinedimethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Dalton Transactions included an article by Wang, Hui-Sheng; Long, Qiao-Qiao; Hu, Zhao-Bo; Yue, Lin; Yang, Feng-Jun; Yin, Cheng-Ling; Pan, Zhi-Quan; Zhang, Yi-Quan; Song, You. Category: alcohols-buliding-blocks. The article was titled 《Synthesis, crystal structures and magnetic properties of a series of chair-like heterometallic [Fe4Ln2] (Ln = GdIII, DyIII, HoIII, and ErIII) complexes with mixed organic ligands》. The information in the text is summarized as follows:

Four chair-like hexanuclear Fe-Ln complexes containing mixed organic ligands, namely, [Fe4Ln2{(py)2CO2}4(pdm)2(NO3)2(H2O)2Cl4]·xCH3CN·yH2O (Ln = GdIII (1, x = 1, y = 0), DyIII (2, x = 1, y = 1), HoIII (3, x = 0, y = 2), and ErIII (4, x = 1, y = 3); (py)2CO2H2 = the gem-diol form of di-2-pyridyl ketone and pdmH2 = 2,6-pyridinedimethanol) were obtained by employing di-2-pyridyl ketone and 2,6-pyridinedimethanol reacting with FeCl3 and Ln(NO3)3 in MeCN. The structures of 1-4 are similar to each other except for the number of lattice solvent mols. Four FeIII and two LnIII in these complexes comprise a chair-like core with the body constructed by four FeIII ions and the end constructed by two LnIII ions. Among the four compounds, 2 shows field-induced single mol. magnet behavior as revealed by a.c. magnetic susceptibility studies, with the effective energy barrier and the pre-exponential factor of 22.07 K and 8.44 × 10-7 s, resp. Ab initio calculations indicated that, among 2_Dy, 3_Ho and 4_Er fragments, the energy gap between the lowest two spin-orbit states for 2_Dy is the largest, while the tunneling gap for 2 is the smallest. These might be the reasons for complex 2 exhibiting SMM behavior. Addnl., the orientations of the magnetic anisotropy of DyIII in 2 were obtained by electrostatic calculations and ab initio calculations, both indicating that the directions of the main magnetic axis of Dy1 ions are almost aligned along Dy1-O5 (O5 from the pdm2- ligand). In the experimental materials used by the author, we found 2,6-Pyridinedimethanol(cas: 1195-59-1Category: alcohols-buliding-blocks)

2,6-Pyridinedimethanol(cas: 1195-59-1) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Organometallics included an article by Eberhardt, Nathan A.; Wellala, Nadeesha P. N.; Li, Yingze; Krause, Jeanette A.; Guan, Hairong. Safety of (4-Bromophenyl)methanol. The article was titled 《Dehydrogenative Coupling of Aldehydes with Alcohols Catalyzed by a Nickel Hydride Complex》. The information in the text is summarized as follows:

A nickel hydride complex, {2,6-(iPr2PO)2C6H3}NiH, has been shown to catalyze the coupling of RCHO and R’OH to yield RCO2R’ and RCH2OH, where the aldehyde also acts as a hydrogen acceptor and the alc. also serves as the solvent. Functional groups tolerated by this catalytic system include CF3, NO2, Cl, Br, NHCOMe, and NMe2, whereas phenol-containing compounds are not viable substrates or solvents. The dehydrogenative coupling reaction can alternatively be catalyzed by an air-stable nickel chloride complex, {2,6-(iPr2PO)2C6H3}NiCl, in conjunction with NaOMe. Acids in unpurified aldehydes react with the hydride to form nickel carboxylate complexes, which are catalytically inactive. Water, if present in a significant quantity, decreases the catalytic efficiency by forming {2,6-(iPr2PO)2C6H3}NiOH, which causes catalyst degradation On the other hand, in the presence of a drying agent, {2,6-(iPr2PO)2C6H3}NiOH generated in situ from {2,6-(iPr2PO)2C6H3}NiCl and NaOH can be converted to an alkoxide species, becoming catalytically competent. The proposed catalytic mechanism features aldehyde insertion into the nickel hydride as well as into a nickel alkoxide intermediate, both of which have been exptl. observed Several mechanistically relevant nickel species including {2,6-(iPr2PO)2C6H3}NiOC(O)Ph, {2,6-(iPr2PO)2C6H3}NiOPh, and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh have been independently synthesized, crystallog. characterized, and tested for the catalytic reaction. While phenol-containing mols. cannot be used as substrates or solvents, both {2,6-(iPr2PO)2C6H3}NiOPh and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh are efficient in catalyzing the dehydrogenative coupling of PhCHO with EtOH. The experimental part of the paper was very detailed, including the reaction process of (4-Bromophenyl)methanol(cas: 873-75-6Safety of (4-Bromophenyl)methanol)

(4-Bromophenyl)methanol(cas: 873-75-6) undergoes three-component reaction with acetylferrocene and arylboronic acid to give ferrocenyl ketones containing biaryls.Safety of (4-Bromophenyl)methanol It is used in the synthesis of amphiphilic, symmetric rod-coil, triblock copolymer of poly(9,9-didodecylfluorene-2,7-diyl) and poly(hydroxyl ethyl methacrylate)

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts