Month: October 2022

The author of 《Photoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols》 were Jana, Sripati; Yang, Zhen; Li, Fang; Empel, Claire; Ho, Junming; Koenigs, Rene M.. And the article was published in Angewandte Chemie, International Edition in 2020. Safety of 3,3,3-Trifluoropropan-1-ol The author mentioned the following in the article:

Hexafluoroisopropanol is typically considered as an unreactive solvent and not as a reagent in organic synthesis. Herein, we report on a mild and efficient photochem. reaction of aryl diazoacetates with hexafluoroisopropanol that enables, under stoichiometric reaction conditions, the synthesis of fluorinated ethers in excellent yield. Mechanistic studies indicate there is a preorganization of hexafluoroisopropanol and the diazoalkane acts as an unreactive hydrogen-bonding complex. Only after photoexcitation does this complex undergo a protonation-substitution reaction to the reaction product. Investigations on the applicability of this photochem. transformation show that a broad variety of acidic alcs. can be subjected to this transformation and thus demonstrate the feasibility of this concept for O-H functionalization reactions (54 examples, up to 98% yield). In the experimental materials used by the author, we found 3,3,3-Trifluoropropan-1-ol(cas: 2240-88-2Safety of 3,3,3-Trifluoropropan-1-ol)

3,3,3-Trifluoropropan-1-ol(cas: 2240-88-2) is a important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.Safety of 3,3,3-Trifluoropropan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Xiao, Haiwen; Shen, Haigen; Zhu, Lin; Li, Chaozhong published an article in Journal of the American Chemical Society. The title of the article was 《Copper-Catalyzed Radical Aminotrifluoromethylation of Alkenes》.Reference of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol The author mentioned the following in the article:

We report herein an unprecedented protocol for aminotrifluoromethylation of alkenes. With Cu(OTf)2 as the catalyst, the reaction of alkenes, (bpy)Zn(CF3)2, and N-fluorobis(benzenesulfonyl)imide (NFSI) at room temperature provides the corresponding aminotrifluoromethylation products in satisfactory yields with high regioselectivity opposite to those driven by CF3 radical addition The method exhibits a broad substrate scope and wide functional group compatibility. A mechanism involving N-radical addition to alkenes followed by trifluoromethylation of alkyl radicals is proposed. The experimental part of the paper was very detailed, including the reaction process of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6Reference of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol)

((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6) is a useful reactant for examining the effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-​II (CA-​II)​. And it is used as chiral auxiliaries in Michael and Aldol addition reactions.Reference of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2013,Ishida, Naoki; Shimamoto, Yasuhiro; Yano, Takaaki; Murakami, Masahiro published 《1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams》.Journal of the American Chemical Society published the findings.Quality Control of Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

In the presence of [Rh(COD)(OH)]2 and the nonracemic bibenzodioxolediphosphine (R)-difluorphos, 1-arylsulfonyl-3-aryl-3-azetidinols such as I (R = Ph, 4-MeOC6H4, 4-F3CC6H4; Ts = 4-MeC6H4SO2) underwent enantioselective rearrangement to give fused thiazinediones such as II (R = Ph, 4-MeOC6H4, 4-F3CC6H4) in 90-95% yields and in 91:9-93:7 er. Stereoselective rearrangement of nonracemic amino acid-derived 1-arylsulfonyl-3-aryl-3-azetidinols such as III (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) in the presence of racemic 2,2′-bis{bis(3,5-xylyl)phosphino}-1,1′-binaphthyl yielded fused dihydrohydroxythiazinediones such as IV (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) as single diastereomers and enantiomers in 97-99% yields. Rearrangement of I (R = Ph) with a perdeuterated tosyl group yielded a deuterated product monolabeled at the N-Me group; a mechanism for the rearrangement is proposed. The structure of IV (R1 = Ph; R2 = Me; R3 = Me; R4 = H) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Quality Control of Azetidin-3-ol hydrochloride)

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.Quality Control of Azetidin-3-ol hydrochloride 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 2015,Wang, Zhaobin; Sheong, Fu Kit; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Sun, Jianwei published 《Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines》.Journal of the American Chemical Society published the findings.Electric Literature of C3H8ClNO The information in the text is summarized as follows:

The first catalytic asym. desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermol. reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combination of catalyst, nucleophile, protective group, and reaction conditions. The highly enantioenriched densely functionalized products are versatile precursors to other useful chiral mols. Mechanistic studies, including DFT calculations, revealed that only one catalyst mol. is involved in the key transition state, though both reactants can be activated. Also, the Curtin-Hammett principle dictates the reaction proceeds via amide nitrogen activation. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6Electric Literature of C3H8ClNO)

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.Electric Literature of C3H8ClNO 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 2015,Kublanovsky, V. S.; Nikitenko, V. N.; Globa, N. I. published 《Effect of the nature of a ligand on electrochemical characteristic of tin films in cycling in lithium-ion batteries》.Russian Journal of Applied Chemistry published the findings.Safety of Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate The information in the text is summarized as follows:

Potentiodynamic and galvanostatic cycling in 1 M ethylene carbonate-dimethyl carbonate solution of LiClO4 were used to study electrolytic tin films deposited from complex (tartrate, citrate, and citrate-trilonate) electrolytes. It was shown that the nature of a ligand strongly affects the electrochem. characteristics, specific capacity of tin films, and efficiency of their cycling in lithium power sources. The most stable charge-discharge characteristics are inherent in tin films deposited from the citrate electrolyte. The results came from multiple reactions, including the reaction of Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate(cas: 6381-59-5Safety of Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate)

Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate(cas: 6381-59-5) is a ferroelectric crystal with a high piezoelectric effect and electromechanical coupling coefficient. Safety of Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate As a Biuret reagent, it is used to measure the protein concentration. Furthermore, it is used as laxative and is also used in food industry.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Park, Sun Jun; Kim, Eunjin; Yoo, Miyoun; Lee, Joo-Youn; Park, Chi Hoon; Hwang, Jong Yeon; Ha, Jae Du published 《Synthesis and biological evaluation of N9-cis-cyclobutylpurine derivatives for use as cyclin-dependent kinase (CDK) inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.Related Products of 27489-62-9 The information in the text is summarized as follows:

A novel 6-aminopurine scaffold bearing an N9-cis-cyclobutyl moiety was designed using structure-based mol. design based on two known CDK inhibitors, dinaciclib and Compound I. A series of novel 6-aminopurine compounds was prepared for structure-activity relationship (SAR) studies of CDK2 and CDK5 inhibitors. Among the compounds synthesized, compound II displayed potent CDK2 and CDK5 inhibitory activities with low nanomolar ranges (IC50 = 2.1 and 4.8 nM, resp.) and showed moderate cytotoxicity in HCT116 colon cancer and MCF7 breast cancer cell lines. Here, we report the synthesis and evaluation of novel 6-aminopurine derivatives and present mol. docking models of compound I with CDK2 and CDK5. The experimental process involved the reaction of trans-4-Aminocyclohexanol(cas: 27489-62-9Related Products of 27489-62-9)

trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Related Products of 27489-62-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Miura, Tomoya; Nakahashi, Junki; Murakami, Masahiro published 《Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid》.Angewandte Chemie, International Edition published the findings.Electric Literature of C13H26B2O4 The information in the text is summarized as follows:

(E)-δ-Boryl-substituted anti-homoallylic alcs. were synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl)alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1: Pd-catalyzed double-bond transposition of the 1,1-di(boryl)alk-3-enes to 1,1-di(boryl)alk-2-enes, 2: chiral phosphoric acid catalyzed allylation of aldehydes, and 3: Pd-catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Electric Literature of C13H26B2O4)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Electric Literature of C13H26B2O4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Tan, Qiuyuan; Wang, Xinqiao; Xiong, Yang; Zhao, Zimeng; Li, Lu; Tang, Pei; Zhang, Min published 《Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers》.Angewandte Chemie, International Edition published the findings.Application of 126456-43-7 The information in the text is summarized as follows:

We have developed a highly efficient asym. allylboration of ketimines with nonchiral γ,γ-disubstituted allylboronic acids by using a chiral amino alc. as the directing group, which is otherwise challenging. The amino alc. not only serves as a cheap source of nitrogen and chirality, but also dramatically enhances the reactivity. The versatility of this method was demonstrated by its ability to access all four stereoisomers with adjacent quaternary carbon centers. A reaction model was proposed to explain the diastereoselectivity and the rate-accelerating effect. The experimental part of the paper was very detailed, including the reaction process of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7Application of 126456-43-7)

(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Application of 126456-43-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,European Journal of Medicinal Chemistry included an article by Pisani, Leonardo; Iacobazzi, Rosa Maria; Catto, Marco; Rullo, Mariagrazia; Farina, Roberta; Denora, Nunzio; Cellamare, Saverio; Altomare, Cosimo Damiano. Formula: C3H7BrO. The article was titled 《Investigating alkyl nitrates as nitric oxide releasing precursors of multitarget acetylcholinesterase-monoamine oxidase B inhibitors》. The information in the text is summarized as follows:

Herein we envisaged the possibility of exploiting alkyl nitrates as precursors of alc.-bearing dual inhibitors targeting acetylcholinesterase (AChE) and monoamine oxidase B (MAO B), key enzymes in neurodegenerative syndromes such as Alzheimer’s disease (AD), through biotransformation unmasking an alc. function upon nitric oxide (NO) release. The cooperation to neuroprotection of low fluxes of NO and target enzymes’ inhibition by the alc. metabolites might return a multitargeting effect. The in vitro screening towards ChEs and MAOs of a collection of 21 primary alcs. disclosed a subset of dual inhibitors, among which three diverse chemotypes were selected to study the corresponding nitrates. Nitrate 14 proved to be a brain permeant, potent AChE-MAO B inhibitor by itself. Moreover, it protected human SH-SY5Y lines against rotenone and hydrogen peroxide with a poor inherent cytotoxicity and showed a slow conversion profile to its alc. metabolite 9d that still behaved as bimodal and neuroprotective mol. After reading the article, we found that the author used 3-Bromopropan-1-ol(cas: 627-18-9Formula: C3H7BrO)

3-Bromopropan-1-ol(cas: 627-18-9) was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and molten salt-polymers. Furthermore, it was used in the synthesis of chiral, quaternary prolines via cyclization of quaternary amino acids.Formula: C3H7BrO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Angewandte Chemie, International Edition included an article by Garreau, Marion; Le Vaillant, Franck; Waser, Jerome. Reference of 3-Bromopropan-1-ol. The article was titled 《C-Terminal bioconjugation of peptides through photoredox catalyzed decarboxylative alkynylation》. The information in the text is summarized as follows:

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. By the use of hypervalent iodine reagents, the introduction of a broad range of functional groups was successful. C-terminal selectivity was achieved by differentiation of the oxidation potentials of the carboxylic acids based on the use of fine-tuned organic dyes. The experimental process involved the reaction of 3-Bromopropan-1-ol(cas: 627-18-9Reference of 3-Bromopropan-1-ol)

3-Bromopropan-1-ol(cas: 627-18-9) was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and molten salt-polymers. Furthermore, it was used in the synthesis of chiral, quaternary prolines via cyclization of quaternary amino acids.Reference of 3-Bromopropan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts