Month: October 2022

Application In Synthesis of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanolOn November 30, 2021 ,《Preparation and pyrolysis of two Amadori analogues as flavor precursors》 appeared in Journal of Analytical and Applied Pyrolysis. The author of the article were Li, Rui; Yin, Xiaoqing; Zhang, Shiyi; Yang, Jinchu; Zhao, Mingqin. The article conveys some information:

Amadori compounds, produced during Maillard reaction, are considered as precursors of flavor compounds On the basis of Amadori compounds, herein two Amadori analogs, di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl alanine ester (A-ARP) and di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl proline ester (P-ARP), were chem. synthesized and their possibility as flavor precursors was evaluated by thermogravimetry (TG), derivative thermogravimetry (DTG), differential scanning calorimetry (DSC), and pyrolysis gas chromatog.-mass spectrometry (Py-GC/MS). TG-DTG analyses indicated that the samples were stable at room temperature, and the largest mass-loss rates (Tp) were at 208 and 278 °C, resp. Upon thermal pyrolysis, the major flavor substances were butan-2-one, Et propionate, furfural, and DL-limonene for A-ARP, while 2,5-dimethylfuran, heptan-2-one, acetophenone, and 1H-pyrrole for P-ARP. The flavor profiles are different from that of corresponding Amadori compounds, and are influenced by pyrolytic temperatures These results provide one method to regulate the species and amounts of the degraded flavor products. Finally, the possible mechanisms of the pyrolytic processes are proposed. In the experimental materials used by the author, we found ((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: 20880-92-6Application In Synthesis 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)​.Application In Synthesis 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 And it is used as chiral auxiliaries in Michael and Aldol addition reactions.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Name: (R)-Oxiran-2-ylmethanolOn October 15, 2019 ,《Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1,2,3-triazole side chain》 was published in European Journal of Medicinal Chemistry. The article was written by Qin, Yinhui; Teng, Yuetai; Ma, Ruixin; Bi, Fangchao; Liu, Zhiyang; Zhang, Panpan; Ma, Shutao. The article contains the following contents:

Macrolides are widely prescribed in clinic to treat various respiratory tract infections. However, due to their inappropriate use, the prevalence of macrolide-resistant strains among clin. isolates has become a concern for public health. Therefore, novel macrolides skeleton structures against resistant pathogens are badly needed. Thus, three series of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1,2,3-triazole side chain were designed and synthesized through creatively opening the ring of clarithromycin (CAM), expanding the ring properly, and introducing a suitable side chain of 1,2,3-triazole at the C12 and C13 positions; they were then evaluated for their antibacterial activity. The antibacterial results indicated that compounds I (R = Q, Q1, Q2) (II) possessed strong antibacterial activity against Staphylococcus aureus ATCC25923 (0.25 μg/mL) and Bacillus subtilis ATCC9372 (0.25 μg/mL). Furthermore, compounds I (R = Q3) (III) and I (R = Q4) (IV) were found to exhibit promising potent activity (8 μg/mL) against Streptococcus pneumonia AB11 expressing the ermB and mefA genes. In addition, the determination of min. bactericidal concentration (MBC) indicated that the most promising compounds II-IV were excellent bacteriostatic agents. The bactericidal curve showed that III exhibited antibacterial activity through bacteriostatic mechanism. Finally, II were confirmed to be non-toxic to MCF-7 breast cancer cells up to a concentration of 32 μg/mL in preliminary cytotoxicity assay. In summary, II-IV can serve as lead compounds to provide a new perspective for further structural optimization. In the part of experimental materials, we found many familiar compounds, such as (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Name: (R)-Oxiran-2-ylmethanol)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Name: (R)-Oxiran-2-ylmethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Category: alcohols-buliding-blocksOn November 1, 2019 ,《Development of theranostic active-targeting boron-containing gold nanoparticles for boron neutron capture therapy (BNCT)》 appeared in Colloids and Surfaces, B: Biointerfaces. The author of the article were Wu, Chun-Yi; Lin, Jia-Jia; Chang, Wen-Yi; Hsieh, Cheng-Ying; Wu, Chin-Ching; Chen, Hong-Sen; Hsu, Hung-Ju; Yang, An-Suei; Hsu, Ming-Hua; Kuo, Wei-Ying. The article conveys some information:

This study aims to develop theranostic AuNP-boron cage assemblies (B-AuNPs) and evaluate its feasibility for BNCT. The com. citrate-coated AuNPs were subjected to PEGylation, azide addition, and carborane modification on the surface. To further arm the AuNPs, we conjugated anti-HER2 antibody (61 IgG) with boron-containing PEGylated AuNPs to form 61-B-AuNPs. The diameter and radiolabeling efficiency of boron-containing AuNPs were determined by dynamic light scattering (DLS) and radio thin-layer chromatog. (radio TLC), resp. Noninvasive single-photon emission computed tomog. (SPECT)/computed tomog. (CT) imaging was performed to determine the pharmacokinetics of radioiodinated AuNPs in N87 gastric cancer xenografts, and the content of boron in tumor and muscle was assessed by inductively coupled plasma mass spectrometry (ICP-MS). After the 3-step modification, the diameter of B-AuNPs increased by ~25 nm, and antibody conjugation did not affect the diameter of AuNPs. Radioactive iodine (I-123) was introduced in AuNPs by Click chem. under copper catalysis. The radiolabeling efficiency of 123I-B-AuNPs and 123I-61-B-AuNPs was approx. 60 ± 5%. After purification, the radiochem. purity (RCP) of these NPs was greater than 90%. MicroSPECT/CT imaging showed that the tumor-to-muscle (T/M) ratio of 123I-B-AuNP-injected mice reached 1.91 ± 0.17 at 12 h post-injection, while that of 123I-61-B-AuNP-injected mice was 12.02 ± 0.94. The experimental part of the paper was very detailed, including the reaction process of 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate(cas: 76931-93-6Category: alcohols-buliding-blocks)

2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate(cas: 76931-93-6) belongs to pyrrolidine. Pyrrolidine being a good nucleophile easily undergoes electrophilic substitution reactions with different electrophiles such alkyl halides and acyl halides, and forms N-substituted pyrrolidines. N-Alkylpyrrolidine on further reaction with alkyl halide provided quaternary salts.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Bogdanov, A. V.; Gazizov, A. S.; Smolobochkin, A. V.; Mironov, V. F. published an article on January 31 ,2019. The article was titled 《Synthesis of New (2-Acetamido)phenylglyoxylamides Containing an Acetal Fragment》, and you may find the article in Russian Journal of Organic Chemistry.Safety of 4,4-Diethoxybutan-1-amine The information in the text is summarized as follows:

Mild opening of the five-membered ring in 1-acetylisatins by the action of an equimolar amount of 4,4-diethoxybutan-1-amine afforded 2-(2-acetamidophenyl)-N-(4,4-diethoxybutyl)-2-oxoacetamides in almost quant. yield. In the experiment, the researchers used 4,4-Diethoxybutan-1-amine(cas: 6346-09-4Safety of 4,4-Diethoxybutan-1-amine)

4,4-Diethoxybutan-1-amine(cas: 6346-09-4) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Safety of 4,4-Diethoxybutan-1-amine

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cai, Aijie; Yan, Wenhao; Wang, Chao; Liu, Wei published their research in Angewandte Chemie, International Edition on December 20 ,2021. The article was titled 《Copper-Catalyzed Difluoromethylation of Alkyl Iodides Enabled by Aryl Radical Activation of Carbon-Iodine Bonds》.Name: ((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 article contains the following contents:

A novel strategy that leveraged the halogen abstraction ability of aryl radicals, thereby engaging a diverse range of alkyl iodides in copper-catalyzed Negishi-type cross-coupling reactions at room temperature Specifically, aryl radicals generated via copper catalysis efficiently initiate the cleavage of the carbon-iodide bonds of alkyl iodides. The alkyl radicals thus generated enter the copper catalytic cycles to couple with a difluoromethyl zinc reagent, thus furnished the alkyl difluoromethane products. This unprecedented Negishi-type difluoromethylation approach was applied to the late-stage modification of densely functionalized pharmaceutical agents and natural products. In the part of experimental materials, we found many familiar compounds, such as ((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: 20880-92-6Name: ((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.Name: ((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

Frey, Guido D.; Rentzsch, Christoph F.; von Preysing, Denise; Scherg, Tobias; Muehlhofer, Michael; Herdtweck, Eberhardt; Herrmann, Wolfgang A. published their research in Journal of Organometallic Chemistry on December 15 ,2006. The article was titled 《N-Heterocyclic carbenes. Part 48. Rhodium and iridium complexes of N-heterocyclic carbenes: Structural investigations and their catalytic properties in the borylation reaction》.Formula: C14H21BO2 The article contains the following contents:

Bridged and unbridged N-heterocyclic carbene (NHC) ligands are metalated with [Ir/Rh(COD)2Cl]2 to give Rh(I/III) and Ir(I) mono- and biscarbene substituted complexes. All complexes were characterized by spectroscopy, and in addition [Ir(COD)(NHC)2][Cl,I] [COD = 1,5-cyclooctadiene, NHC = 1,3-dimethyl- or 1,3-dicyclohexylimidazolin-2-ylidene] (1, 4, resp.), and the bis(carbene) chelate complexes [(η4-1,5-cyclooctadiene)(1,1′-di-n-butyl-3,3′-ethylene-diimidazolin-2,2′-diylidene)iridium(I) bromide] (12) and [(η4-1,5-cyclooctadiene)(1,1′-dimethyl-3,3′-o-xylylene-diimidazolin-2,2′-diylidene)iridium(I) bromide] (14) were characterized by single crystal x-ray anal. The relative σ-donor/π-acceptor qualities of various NHC ligands were examined and classified in monosubstituted NHC-Rh and NHC-Ir dicarbonyl complexes by IR spectroscopy. For the 1st time, bis(carbene)-substituted Ir complexes were used as catalysts in the synthesis of arylboronic acids starting from pinacolborane and arene derivatives2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Formula: C14H21BO2) was used in this study.

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. 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.Formula: C14H21BO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2015,Chemistry – A European Journal included an article by Vidal-Ferran, Anton; Mon, Ignasi; Bauza, Antonio; Frontera, Antonio; Rovira, Laura. Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol. The article was titled 《Supramolecularly Regulated Ligands for Asymmetric Hydroformylations and Hydrogenations》. The information in the text is summarized as follows:

The use of polyether binders as regulation agents (RAs) to enhance the enantioselectivity of rhodium-catalyzed transformations has been reported. For reactions of diverse substrates mediated by rhodium complexes of the α,ω-bisphosphite-polyether ligands such as I [X = (OCH2CH2)3], the enantiomeric excess (ee) of hydroformylations was increased by up to 82% (substrate: vinyl benzoate, 96% ee), and the ee value of hydrogenations was increased by up to 5% (substrate: N-(1-(naphthalene-1-yl)vinyl)acetamide, 78% ee). The ligand design enabled the regulation of enantioselectivity by generation of an array of catalysts that simultaneously preserve the advantages of a privileged structure in asym. catalysis and offer geometrically close catalytic sites. The highest enantioselectivities in the hydroformylation of vinyl acetate with a tetra(ethylene glycol) bis(binaphthylphosphite) were achieved by using the Rb[B(3,5-(CF3)2C6H3)4] (RbBArF) as the RA. The enantioselective hydrogenation of alkenes R1CH=C(R2)(XC(O)G) [R1 = H, Ph; R2 = CO2CH3, 1-naphthyl; X = CH2, NH, NHCH2; G = OMe, C(O)Me] required rhodium catalysts derived from either a biphenylbis(tetra(ethylene glycol)) bis(binaphthylphosphite) or a tetra(ethylene glycol) bis(binaphthylphosphite) either alone or in combination with different RAs (sodium, cesium, or (R,R)-bis(1-phenylethyl)ammonium salts). This design approach was supported by results from computational studies.(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) was used in this study.

(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).Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Beilstein Journal of Organic Chemistry included an article by Liu, Xinyun; Phan, Johnny H.; Haugeberg, Benjamin J.; Londhe, Shrikant S.; Clift, Michael D.. Synthetic Route of C9H13NO. The article was titled 《Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols》. The information in the text is summarized as follows:

A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcs. is reported. A wide range of readily accessible amino alcs. and primary amines can be reacted to provide N-protected imine products. The methodol. presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage. The results came from multiple reactions, including the reaction of 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. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Synthetic Route of C9H13NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2021,Indian Journal of Pharmaceutical Sciences included an article by Xie, Jing; Qin, Yeyu; Wang, Min; Wu, Danna; Zhong, Lili; Zhang, J.. SDS of cas: 23828-92-4. The article was titled 《Effects of ambroxol hydrochloride on lung tissue cell apoptosis and vascular remodeling in rats with smoke induced chronic obstructive pulmonary disease》. The information in the text is summarized as follows:

To evaluate the effects of ambroxol hydrochloride on lung tissue cell apoptosis and vascular remodeling in rats with smoke induced chronic obstructive pulmonary disease. Sprague Dawley rats were randomly divided into normal, model, exptl. and control groups (n=20). The rat model of chronic obstructive pulmonary disease was established by fumigation using Yan′an Cigarettes for 64 d. After fumigation, the exptl. and control groups were s.c. injected with 5 mL of Ambroxol hydrochloride (20 mg/kg) and 5 mL of Bambuterol hydrochloride (20 mg/kg) resp., while the normal and model groups were i.p. injected with an equal dose of normal saline. Following drug intervention for 28 d, the pathol. changes in lung tissues, vascular remodeling, lung tissue cell apoptosis, expressions of alpha-smooth muscle actin and vascular endothelial growth factor, as well as levels of caspase-3, B-cell lymphoma-2 and B-cell lymphoma-2 associated X protein were detected by hematoxylin and eosin staining, elastic Van Gieson staining, terminal deoxynucleotidyl transferase dUTP nick end labeling staining, immunohistochem. staining and western blotting, resp. Compared with normal group, the damage of lung tissues was obvious, the medial thickness of pulmonary arterioles significantly increased, the degree of vascular muscularization, apoptosis rate and expressions of alpha-smooth muscle actin, vascular endothelial growth factor, caspase-3 and B-cell lymphoma-2 associated X protein rose and the expression of B-cell lymphoma-2 decreased in model group (p<0.05). Compared with model group, the damage of lung tissues was significantly improved, the medial thickness of pulmonary arterioles decreased, the degree of vascular muscularization, apoptosis rate and expressions of alpha-smooth muscle actin, vascular endothelial growth factor, caspase-3 and B-cell lymphoma-2 associated X protein reduced and the expression of B-cell lymphoma-2 rose in exptl. and control groups (p<0.05). Ambroxol hydrochloride can inhibit the apoptosis of lung tissue cells and improve vascular remodeling, thereby protecting the lung tissues of chronic obstructive pulmonary disease rats. In the experimental materials used by the author, we found trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride(cas: 23828-92-4SDS of cas: 23828-92-4)

trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride(cas: 23828-92-4) is a medication indicated to alleviate chest congestion associated with conditions that include bronchitis, pneumonia, bronchospasm asthma, cough, and allergy.SDS of cas: 23828-92-4 Preclinically, ambroxol, the active ingredient of Mucosolvan, has been shown to increase respiratory tract secretion.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ren, Xinyi; Wang, Zhen; Shen, Chaoren; Tian, Xinxin; Tang, Lin; Ji, Xiaolei; Dong, Kaiwu published their research in Angewandte Chemie, International Edition on August 2 ,2021. The article was titled 《Asymmetric Alkoxy- and Hydroxy-Carbonylations of Functionalized Alkenes Assisted by β-Carbonyl Groups》.Category: alcohols-buliding-blocks The article contains the following contents:

As a fundamental type of carbonylation reaction, the alkoxy- and hydroxy-carbonylation of unsaturated hydrocarbons constitutes one of the most important industrial applications of homogeneous catalysis. However, owing to the difficulties in controlling multi-selectivities for asym. hydrocarbonylation of alkenes, this reaction is typically limited to vinylarenes and analogs. In this work, a highly efficient asym. alkoxy- and hydroxy-carbonylation of β-carbonyl functionalized alkenes was developed, providing practical and easy access to various densely functionalized chiral mols. with high optical purity from broadly available alkenes, CO, and nucleophiles (>90 examples, 84-99% ee). This protocol features mild reaction conditions and a broad substrate scope, and the products can be readily transformed into a diverse array of chiral heterocycles. Control experiments revealed the key role of the β-carbonyl group in determining the enantioselectivity and promoting the activity, which facilitates chiral induction by coordination to the transition metal as rationalized by DFT calculations The strategy of utilizing an innate functional group as the directing group on the alkene substrate might find further applications in catalytic asym. hydrocarbonylation reactions. In the experiment, the researchers used ((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: 20880-92-6Category: alcohols-buliding-blocks)

((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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts