Month: February 2023

Chiral Bis(NHC)-Palladium(II) Complex Catalyzed and Diethylzinc-Mediated Enantioselective Umpolung Allylation of Aldehydes was written by Wang, Wenfeng;Zhang, Tao;Shi, Min. And the article was included in Organometallics in 2009.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

A series of chiral bis(NHC)-Pd(II) complexes bearing different coordinating counterions have been prepared and successfully applied in Et₂Zn-mediated enantioselective umpolung allylation of aldehydes with cyclohexenyl acetate, affording the homoallylic alcs. in moderate to excellent yields (up to 96%), modest enantioselectivities (54%-66% ee), and good to excellent syn diastereoselectivities (up to 99:1 dr). In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Activity Relationship Probing of the Natural Marine Antifoulant Barettin was written by Labriere, Christophe;Cervin, Gunnar;Pavia, Henrik;Hansen, Joern H.;Svenson, Johan. And the article was included in Marine Biotechnology in 2021.Category: bromides-buliding-blocks This article mentions the following:

In the current study the antifouling activity of 29 synthetic analogs e.g., I designed and inspired by the potent antifouling effect seen for benzo[g]dipodazine were reported. The library contains mainly not only dipodazine derivatives but also disubstituted diketopiperazines and compounds incorporating alternative heterocyclic cores such as hydantoin, creatinine, and rhodanine. Several of the prepared compounds inhibit the settlement of Amphibalanus improvisus cyprids at low micromolar concentrations, in parity with the natural barettin. While several highly active compounds were prepared by incorporating the benzo[g]indole as hydrophobic substituent, the remarkable antifouling effect reported for benzo[g]dipodazine was not observed when evaluated in the study. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Category: bromides-buliding-blocks).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Structure-Activity Relationships of Stilbene Retinoid Analogs Substituted with Heteroaromatic Carboxylic Acids was written by Beard, Richard L.;Colon, Diana F.;Gillett, Samuel J.;Henry, Elizabeth;Marler, Deborah K.;Song, Tae;Denys, Lydia;Garst, Michael E.;Arefieg, Taghreed. And the article was included in Journal of Medicinal Chemistry in 1995.Computed Properties of C8H7BrO2 This article mentions the following:

Retinoids elicit biol. responses by activating a series of nuclear receptors. Six retinoid receptors belonging to two families are currently known: retinoic acid receptors (RAR_{浼?灏?and绾?/sub>) and retinoid X receptors (RXR浼?灏?and绾?/sub>). Stilbene retinoid analogs of retinoic acid (RA), such as (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propen-1-yl]benzoic acid (TTNPB) and (E)-4-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)propen-1-yl]benzoic acid (3-methyl-TTNPB) (I), display differential RAR and RXR activities, depending on the substituent at C3 of the naphthalene ring. The authors report here structural modifications of the benzoate moiety of I that result in analogs with greater RXR selectivity as well as those with pan-agonist (activate both RAR and RXR receptors) activities, analyze the structural features that impart receptor selectivity, and describe a stereoselective method for the synthesis of these analogs. The biol. activities associated with the RAR and RXR receptors were examined by testing representative examples with different receptor activation profiles for their ability to induce tissue transglutaminase (Tgase) activity in a human promyelocytic leukemia cell line (HL-60 cdm-1) and to inhibit tumor-promoter-induced ornithine decarboxylase (ODC) activity in hairless mouse skin. These results suggest that RAR agonists and RXR agonists may have different therapeutic applications. Finally, the authors show that RXR agonists are significantly reduced in teratogenic potency relative to RAR agonists and may therefore have significant advantages in clin. practice. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Computed Properties of C8H7BrO2).}

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Computed Properties of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation was written by Zhong, Dayou;Wu, Di;Zhang, Yan;Lu, Zhiwu;Usman, Muhammad;Liu, Wei;Lu, Xiuqiang;Liu, Wen-Bo. And the article was included in Organic Letters in 2019.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chem. A direct synthesis of sultams by an intramol. C(sp³)-H amidation reaction using an iron complex in situ derived from Fe(ClO₄)₂ and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-activity relationship study of pyridazine derivatives as glutamate transporter EAAT2 activators was written by Xing, Xuechao;Chang, Ling-Chu;Kong, Qiongman;Colton, Craig K.;Lai, Liching;Glicksman, Marcie A.;Lin, Chien-Liang Glenn;Cuny, Gregory D.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.SDS of cas: 83902-02-7 This article mentions the following:

Excitatory amino acid transporter 2 (EAAT2) is the major glutamate transporter and functions to remove glutamate from synapses. A thiopyridazine derivative I (R = 2-Cl-6-FC₆H₃CH₂) has been found to increase EAAT2 protein levels in astrocytes. A structure-activity relationship study revealed that several components of the mol. were required for activity, such as the thioether and pyridazine. Modification of the benzyl thioether resulted in compounds I (R = 2,4-Me₂C₆H₄CH₂, 2,6-Me₂C₆H₃CH₂, 2-Cl-6-FC₆H₃CH₂CH₂) that enhanced EAAT2 levels by >6-fold at concentrations <5 娓璏 after 24 h. In addition, the compound I (R = 2,6-Cl₂C₆H₃CH₂) enhanced EAAT2 levels 3.5-3.9-fold after 24 h with an EC₅₀ of 0.5 娓璏. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7SDS of cas: 83902-02-7).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.SDS of cas: 83902-02-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Polycyclic heteroaromatics via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis was written by Cho, Eun Kee;Quach, Phong K.;Zhang, Yunfei;Sim, Jae Hun;Lambert, Tristan H.. And the article was included in Chemical Science in 2022.Application of 85118-24-7 This article mentions the following:

The use of hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described. In particular, substrates bearing Lewis basic functionalities such as pyridine rings and amines, which strongly inhibit acid catalyzed RCCOM reactions, are shown to be compatible with this reaction. Using 5 mol% catalyst loadings, a variety of PHA structures can be synthesized from biaryl alkenyl aldehydes, which themselves are readily prepared by cross-coupling. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application of 85118-24-7).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 85118-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

GC-MS analysis of fatty acids of Irvingia gabonensis seed fat was written by Okore, V. C.;Udeala, O. K.. And the article was included in Nigerian Journal of Natural Products and Medicine in 1997.Quality Control of 15-Bromopentadecanoic acid This article mentions the following:

Dika fat is the name given to the waxy material obtained from the seeds of Irvingia gabonensis (Fam. Irvingiaceae). The fat has been a subject of research in recent years, and it has been evaluated as a component of different drug delivery systems . Despite the impressive properties of this wax as have been established in the earlier studies, information on its chem. composition is rather scanty. Chem. characterization of the wax was done by GC-MS technique. The dika fat was obtained by solvent extraction, using the method described by Udeala et al (1980). A Fisons Trio 200 Quadrupole GC-MS instrument fitted with a 30m 鑴?0.32mm (i.d.) OV-1 capillary column, was used for the anal. The column temperature was programmed to rise from 100鎺矯 to 280鎺矯 at the rate of 5鎺?min. The carrier gas was helium flowing at the rate of 1.5ml/min. Ionization voltage of 70eV was applied. The solvent for dika fat was n-hexane. The identity of the components of dika fat was confirmed by a combination of computer-aided identification, the eight peak index of mas spectra as well as co-chromatog. The gas chromatogram of dika fat reveals seven peaks representing major components and about the same number of peaks for the minor components. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Quality Control of 15-Bromopentadecanoic acid).

15-Bromopentadecanoic acid (cas: 56523-59-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of 15-Bromopentadecanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Formation of C(sp²)-boronate esters by borylative cyclization of alkynes using BCl₃ was written by Warner, Andrew J.;Lawson, James R.;Fasano, Valerio;Ingleson, Michael J.. And the article was included in Angewandte Chemie, International Edition in 2015.Computed Properties of C9H11BrO This article mentions the following:

Arylpropargyl compounds R¹C₆H₄YCH₂C椤氬挵R² undergo cyclization in a reaction with BCl₃ and pinacol, yielding cyclic alkenylboronates I (2, R¹ = H, Me, MeO, Cl; Y = CH₂, NTs, O; R² = Ph, ClC₆H₄, C₆F₅, 3-CF₃C₆H₄, 4-NCC₆H₄, MeC₆H₄, Br, Me, 1-naphthyl, PhCH:CH, 4-NO₂C₆H₄, 4-EtO₂CC₆H₄). Diynes R³C椤氬挵CH₂YCH₂C椤氬挵R³ gave boronates II (R³ = Ph, 10a,b; Y = CH₂, NTs) or III (11, R³ = H, Y = CH₂). BCl₃ is an inexpensive electrophile which induces the borylative cyclization of a wide range of substituted alkynes to regioselectively form polycycles containing synthetically versatile C(sp²)-boronate esters. It proceeds rapidly, with good yields and is compatible with a range of functional groups and substitution patterns. Intermol. 1,2-carboboration of alkynes Ar¹C椤氬挵Me is also achieved using BCl₃ and arene Ar²H to generate trisubstituted vinyl boronate esters Ar¹Ar²C:CMe(Bpin) (12, Ar¹ = Ph, Ar² = 5-methyl-2-thienyl). In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Computed Properties of C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon鑱砨romine bond is electrophilic in nature. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Computed Properties of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature was written by Mei, Chong;Zhao, Mengdi;Lu, Wenjun. And the article was included in Journal of Organic Chemistry in 2021.Category: bromides-buliding-blocks This article mentions the following:

Here, in a palladium/oxidant/acid catalytic system at room temperature, one arene could highly selectively couple with the other one to afford the target unsym. biaryls just by controlling the directing groups and the substituted groups on their Ph rings was reported. The utility of this one-one cross-coupling was also demonstrated by synthesis of a few bioactive mols. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Category: bromides-buliding-blocks).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon鑱砨romine bond is electrophilic in nature. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Inhibition of tyrosine phenol-lyase by tyrosine homologues was written by Do, Quang;Nguyen, Giang T.;Phillips, Robert S.. And the article was included in Amino Acids in 2016.Formula: C9H11BrO This article mentions the following:

The authors designed, synthesized, and evaluated tyrosine homologs and their O-Me derivatives as potential inhibitors for tyrosine phenol-lyase (TPL; EC 4.1.99.2). Recently, the authors reported that homologs of tryptophan were potent inhibitors of tryptophan indole-lyase (tryptophanase; TIL, EC 4.1.99.1), with K_i values in the low micromolar range. As the structure and mechanism for TPL is very similar to that of TIL, the authors postulated that tyrosine homologs could also be potent inhibitors of TPL. However, the authors found that homotyrosine, bishomotyrosine, and their corresponding O-Me derivatives were competitive inhibitors of TPL, which exhibited K_i values in the range of 0.8-1.5 mM. Thus, these compounds were not potent inhibitors, but instead bound with affinities similar to common amino acids, such as phenylalanine or methionine. Pre-steady-state kinetic data were very similar for all compounds tested and demonstrated the formation of an equilibrating mixture of aldimine and quinonoid intermediates upon binding. Interestingly, the authors also observed a blue-shift for the absorbance peak of external aldimine complexes of all tyrosine homologs, suggesting possible strain at the active site due to accommodating the elongated side-chains. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary