Month: October 2022

Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diolOn October 18, 2004 ,《Synthesis and characterization of alkyllanthanum biphenolate complexes as catalysts for hydroamination/cyclization and hydrosilylation》 was published in European Journal of Inorganic Chemistry. The article was written by Gribkov, Denis V.; Hampel, Frank; Hultzsch, Kai C.. The article contains the following contents:

The homochiral, dimeric biphenolate alkyllanthanum complex [La{(R)-Biphen}{CH(SiMe3)2}]2 can be prepared by facile alkane elimination starting from [La{CH(SiMe3)2}3] and enantiopure (R)-3,3′-di-tert-butyl-5,5′,6,6′-tetramethyl-1,1′-biphenyl-2,2′-diol [H2{(R)-Biphen}]. Single-crystal x-ray diffraction revealed that the two La{(R)-Biphen}{CH(SiMe3)2} fragments are connected through bridging phenolate groups of the biphenolate ligands. The two different phenolate groups undergo an intramol. exchange process in solution leading to their equivalence on the NMR time scale. The biphenolate alkyl complex shows high catalytic activity for hydroamination/cyclization of aminoalkenes, similar to previously known lanthanocene catalysts, but only low enantio-selectivity. Addition of THF to [La{(R)-Biphen}{CH(SiMe3)2}]2 leads to a monomeric tris-THF adduct [La{(R)-Biphen}{CH(SiMe3)2}(THF)3] with higher catalytic activity than the THF-free homochiral dimer in the cyclization of 2,2-dimethylpent-4-enylamine, suggesting that the dimeric structure of the catalyst system prevails under catalytic conditions in the absence of THF. Addition of HN(SiHMe2)2 to [La{(R)-Biphen}{CH(SiMe3)2}(THF)3] results in the formation of [La{(R)-Biphen}{N(SiHMe2)2}(THF)3] which is in equilibrium with its homochiral dimer [La{(R)-Biphen}{N(SiHMe2)2}(THF)]2 at elevated temperatures The biphenolate alkyl complexes exhibit good catalytic activity and diastereoselectivity in the hydrosilylation of styrene. Hydrosilylation of 1-hexene and norbornene also proceeds with high diastereoselectivity but rather low activity. In the part of experimental materials, we found many familiar compounds, such as (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraolOn September 15, 2019 ,《A polysaccharide found in Dendrobium nobile Lindl stimulates calcium signaling pathway and enhances tobacco defense against TMV》 was published in International Journal of Biological Macromolecules. The article was written by Li, Zhurui; Shi, Jing; Hu, Deyu; Song, Baoan. The article contains the following contents:

A neutral polysaccharide separated from Dendrobium nobile Lindl was designated as DNPE6(4). It was structurally characterized using a combination of spectral and chem. anal. Its average mol. weight was 99.2 kDa. The monosaccharide composition was Araf, Glcp, Galp, and Manp in a molar ratio of 2.5:0.9:0.3:0.8. Their linkage types were (→1)-L-Araf-(3→, →1)-D-Glcp-(4→, →1)-D-Galp-(3→, →1)-D-Galp-(6→, →1)-D-Manp-(3, 6→), and T-D-Manp. The polysaccharide was found to have anti-TMV and anti-CMV activities for the first time in vivo. Notably, DNPE6(4) exhibited excellent protective activity against TMV. Furthermore, several proteins related to calcium signaling pathway and pathogen related proteins were up-regulated, and we also found expression levels of EDS1, ICS1, and PR1 involved in SA pathway up-regulated after DNPE6(4) treatment. In addition, some defense enzymes increased in the same condition. All these findings revealed DNPE6(4) was an elicitor to stimulate calcium signaling pathway to enhance the tobacco defense against TMV. This study therefore revealed that DNPE6(4) was a promising antiviral agent for future study. In the experiment, the researchers used rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(cas: 54-17-1Reference of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol)

rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(cas: 54-17-1) is oxidized in various tissues under either aerobic or anaerobic conditions through glycolysis; the oxidation reaction produces carbon dioxide, water, and ATP.Reference of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Bagutski, Viktor; Del Grosso, Alessandro; Carrillo, Josue Ayuso; Cade, Ian A.; Helm, Matthew D.; Lawson, James R.; Singleton, Paul J.; Solomon, Sophia A.; Marcelli, Tommaso; Ingleson, Michael J. published an article on January 9 ,2013. The article was titled 《Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis》, and you may find the article in Journal of the American Chemical Society.Application of 401797-00-0 The information in the text is summarized as follows:

Direct electrophilic borylation using Y2BCl (Y2 = Cl2 or o-catecholato) with equimolar AlCl3 and a tertiary amine has been applied to a wide range of arenes and heteroarenes, yielding aryl and heterocyclic boronates in a regioselective way. In situ functionalization of the ArBCl2 products is possible with Me3SiOCOCH2NMeCH2CO2SiMe3 (TMS2MIDA), to afford bench-stable and easily isolable MIDA-boronates in moderate to good yields; pinacol and neopentylglycol esters were also prepared According to a combined exptl. and computational study, the borylation of activated arenes at 20° proceeds through an SEAr mechanism with borenium cations, [Y2B(amine)]+, the key electrophiles. For catecholato-borocations, two amine dependent reaction pathways were identified: with [CatB(NEt3)]+, an addnl. base is necessary to accomplish rapid borylation by deprotonation of the borylated arenium cation (σ complex), which otherwise would rather decompose to the starting materials than liberate the free amine to effect deprotonation. Apart from amines, the addnl. base may also be the arene itself when it is sufficiently basic (e.g., N-Me-indole). When the amine component of the borocation is less nucleophilic (e.g., 2,6-lutidine), no addnl. base is required due to more facile amine dissociation from the boron center in the borylated arenium cation intermediate. Borenium cations do not borylate poorly activated arenes (e.g., toluene) even at high temperatures; instead, the key electrophile in this case involves the product from interaction of AlCl3 with Y2BCl. When an extremely bulky amine is used, borylation again does not proceed via a borenium cation; instead, a number of mechanisms are feasible including via a boron electrophile generated by coordination of AlCl3 to Y2BCl, or by initial (heteroarene)AlCl3 adduct formation followed by deprotonation and transmetalation. In the experimental materials used by the author, we found 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Application of 401797-00-0)

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this functional group.Application of 401797-00-0 Organic compounds, which are often poorly soluble in water, become water-soluble when they contain two or more hydroxy groups, as illustrated by sugars and amino acid.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gutierrez, Elisa G.; Moorhead, Eric J.; Smith, Eva H.; Lin, Vivian; Ackerman, Laura K. G.; Knezevic, Claire E.; Sun, Victoria; Grant, Sharday; Wenzel, Anna G. published an article in European Journal of Organic Chemistry. The title of the article was 《Electron-Withdrawing, Biphenyl-2,2′-diol-Based Compounds for Asymmetric Catalysis》.Application of 329735-68-4 The author mentioned the following in the article:

Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′-diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphonylation of N-(2-methoxyphenyl) benzaldimine and the Friedel-Crafts alkylation of indole with chalcone was investigated. In the latter reaction, the chloro-substituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date. The results came from multiple reactions, including the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Application of 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Application of 329735-68-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hultzsch, Kai C.; Jernelius, Jesper A.; Hoveyda, Amir H.; Schrock, Richard R. published an article on February 15 ,2002. The article was titled 《The first polymer-supported and recyclable chiral catalyst for enantioselective olefin metathesis》, and you may find the article in Angewandte Chemie, International Edition.Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The information in the text is summarized as follows:

The synthesis of polymer-bound [(1R)-3,3′-Bis(1,1-dimethylethyl)-6,6′-tetramethyl[1,1′-biphenyl]-2,2′-diolato(2-)-κO,κO’][2,6-bis(1-methylethyl)benzenaminato(2-)](2-methyl-2-phenylpropylidene)molybdenum (I) from [2,6-bis(1-methylethyl)benzenaminato(2-)][1,2-di(methoxy-κO)ethane](2-methyl-2-phenylpropylidene)bis(trifluoromethanesulfonato-κO)molybdenum and a chiral polymer-bound [1,1′-biphenyl]-2,2′-diol precursor was reported. The activity of the polymer-bound catalyst I was compared to un-supported [(1R)-3,3′-bis(1,1-dimethylethyl)-5,5′,6,6′-tetramethyl[1,1′-biphenyl]-2,2′-diolato(2-)-κO,κO’][2,6-bis(1-methylethyl)benzenaminato(2-)](2-methyl-2-phenylpropylidene)molybdenum in metathesis reactions of several alkenes. After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2015,Organic & Biomolecular Chemistry included an article by Bheeter, Charles Beromeo; Chowdhury, Abhishek Dutta; Adam, Rosa; Jackstell, Ralf; Beller, Matthias. Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The article was titled 《Efficient Rh-catalyzed C-H borylation of arene derivatives under photochemical conditions》. The information in the text is summarized as follows:

Photocatalysis allows innovations in organic synthesis. Among the various catalytic reactions, CH-functionalizations offer valuable possibilities for the refinement of easily available building blocks. In this respect, catalytic borylation is of interest, too. So far, most of the catalytic borylation reactions are performed under thermal conditions at comparably high temperatures Here, authors describe a new synthetic route for efficient borylation reactions of arenes using a photocatalytic pathway. This novel approach allows the synthesis of a broad variety of borylated arenes and heteroarenes under mild conditions. Applying trans-[Rh(PMe3)2(CO)Cl] as an active photocatalyst and HBPin as an boron source, authors achieved high TON. A catalytic cycle that relies on a Rh(i)-Rh(iii) interconversion is proposed. In the experiment, the researchers used many compounds, for example, 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this functional group.Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Organic compounds, which are often poorly soluble in water, become water-soluble when they contain two or more hydroxy groups, as illustrated by sugars and amino acid.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ishiyama, Tatsuo; Takagi, Jun; Ishida, Kousaku; Miyaura, Norio; Anastasi, Natia R.; Hartwig, John F. published an article on January 23 ,2002. The article was titled 《Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate》, and you may find the article in Journal of the American Chemical Society.Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The information in the text is summarized as follows:

The borylation of arenes leads to the formation of synthetically versatile products from unactivated arene reagents. It is reported that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions. These reactions encompass arenes bearing both electron-withdrawing and electron-donating substituents. The temperatures required for the transformation are much lower than those previously reported for direct arene borylation. The combination of [Ir(COE)2Cl]2 and (4,4-di-t-butyl)bipyridine even allows for reaction at room temperature The same catalyst system at 100° provides remarkably high turnover numbers for a hydrocarbon functionalization process. Mechanistic studies show that the reactions involve uncommon, Ir(II) tris-boryl complexes. An example of this type of complex ligated by di-t-butylbipyridine, [Ir(COE)(Bpin)3(4,4′-di-t-Bu-BPY)], was isolated and structurally characterized. It reacted rapidly at room temperature to produce aryl boronate esters in high yields. In the part of experimental materials, we found many familiar compounds, such as 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kushwaha, Pragati; Tripathi, Ashish Kumar; Gupta, Sampa; Kothari, Priyanka; Upadhyay, Akanksha; Ahmad, Naseer; Sharma, Tanuj; Siddiqi, M. I.; Trivedi, Ritu; Sashidhara, Koneni V. published their research in European Journal of Medicinal Chemistry on August 5 ,2018. The article was titled 《Synthesis and study of benzofuran-pyran analogs as BMP-2 targeted osteogenic agents》.Application of 153759-59-2 The article contains the following contents:

Twenty-four novel benzofuran-pyran derivatives were synthesized and evaluated for their anti-osteoporotic activity in primary cultures of rat calvarial osteoblasts in vitro. Among all the compounds screened for the alk. phosphatase activity, three compounds 9-(2-(4-fluorobenzoyl)-7-methylbenzofuran-5-yl)3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione , 9-(7-Ethyl-2-(4-fluorobenzoyl)benzofuran-5-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione and 9-(7-Ethyl-2-(4-fluorobenzoyl)benzofuran-5-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione showed potent activity at picomolar concentrations in osteoblast differentiating stimulation. Addnl., these compounds were found effective in mineralization, assessed by alizarin red-S staining assay. Compounds were again validated through a series of other in vitro experiments Moreover, mol. dynamics simulations demonstrated that both benzofuran and pyran moieties are requisite to fit into the active site of BMP-2 receptor, a key target of the osteogenic agents. The obtained results strongly convey that compound 9-(2-(4-fluorobenzoyl)-7-methylbenzofuran-5-yl)3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione is a potential bone anabolic agent among synthesized series, which can be further explored as a drug lead for treating osteoporosis. After reading the article, we found that the author used 5-(tert-Butyl)-4-hydroxyisophthalaldehyde(cas: 153759-59-2Application of 153759-59-2)

5-(tert-Butyl)-4-hydroxyisophthalaldehyde(cas: 153759-59-2) belongs to phenols.Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides (aryloxides according to the IUPAC Gold Book).Application of 153759-59-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Pajouhesh, Hassan; Feng, Zhong-Ping; Ding, Yanbing; Zhang, Lingyun; Pajouhesh, Hossein; Morrison, Jerrie-Lynn; Belardetti, Francesco; Tringham, Elizabeth; Simonson, Eric; Vanderah, Todd W.; Porreca, Frank; Zamponi, Gerald W.; Mitscher, Lester A.; Snutch, Terrance P. published an article on February 15 ,2010. The article was titled 《Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol The information in the text is summarized as follows:

A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 (I) exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain. The results came from multiple reactions, including the reaction of (3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol)

(3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Schaus, Scott E.; Brandes, Bridget D.; Larrow, Jay F.; Tokunaga, Makoto; Hansen, Karl B.; Gould, Alexandra E.; Furrow, Michael E.; Jacobsen, Eric N. published an article on February 20 ,2002. The article was titled 《Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIII Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols》, and you may find the article in Journal of the American Chemical Society.Recommanded Product: (1S)-1-(2-chlorophenyl)ethane-1,2-diol The information in the text is summarized as follows:

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by a chiral (salen)CoIII complex affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, com. available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200. The experimental part of the paper was very detailed, including the reaction process of (1S)-1-(2-chlorophenyl)ethane-1,2-diol(cas: 133082-13-0Recommanded Product: (1S)-1-(2-chlorophenyl)ethane-1,2-diol)

(1S)-1-(2-chlorophenyl)ethane-1,2-diol(cas: 133082-13-0) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The creation of a peptide bond to link two amino acids to make a protein removes the −OH from the carboxy group of one amino acid.Recommanded Product: (1S)-1-(2-chlorophenyl)ethane-1,2-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts