Name: N3-1,4-trans-CHC-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

trans-4-azidocyclohexanecarboxylic acid

Melting Point

70-72°C

Appearance

White crystalline powder

Storage

Store at 2-8 °C

N3-1,4-trans-CHC-OH is a chemical compound with unique structural and functional properties, offering various applications in scientific research and industry. Here are some key applications of N3-1,4-trans-CHC-OH:

Medicinal Chemistry: N3-1,4-trans-CHC-OH is studied in medicinal chemistry for its potential pharmacological properties. Researchers explore its role as a building block in synthesizing pharmaceutical compounds with therapeutic benefits. Its structure may contribute to the development of new drugs targeting specific biochemical pathways.

Organic Synthesis: This compound is valuable in organic synthesis as an intermediate for creating complex chemical structures. Chemists use it to introduce specific functional groups into target molecules, facilitating the synthesis of more intricate compounds. Its versatility in reactions makes it a useful component in synthetic chemistry.

Catalysis Studies: N3-1,4-trans-CHC-OH is investigated for its potential as a catalyst or catalyst precursor in various chemical reactions. Its unique molecular attributes can influence reaction kinetics and selectivity, offering opportunities for more efficient and sustainable chemical processes. This application is crucial in developing greener industrial practices.

Material Science: In material science, N3-1,4-trans-CHC-OH can be used as a precursor for creating novel polymers and advanced materials. Its incorporation into material matrices may enhance their physical and chemical properties such as conductivity or mechanical strength. These enhanced materials can be applied in electronics, construction, and other fields demanding high-performance substances.

1. Photochemical generation and the reactivity of o-naphthoquinone methides in aqueous solutions

Selvanathan Arumugam, Vladimir V Popik J Am Chem Soc. 2009 Aug 26;131(33):11892-9. doi: 10.1021/ja9031924.

Irradiation of 3-hydroxy-2-naphthalenemethanol (3a) and 2-hydroxy-1-naphthalenemethanol (4a) results in efficient (Phi(254) = 0.17 and 0.20) dehydration and the formation of isomeric naphthoquinone methides, 2,3-naphthoquinone-3-methide (1) and 1,2-naphthoquinone-1-methide (2), respectively. In aqueous solution, naphthoquinone methides 1 and 2 undergo rapid hydration to regenerate starting materials (tau(H2O) (1) = 7.4 ms and tau(H2O) (2) = 4.5 ms at 25 degrees C). The hydration reaction is strongly catalyzed by the hydroxide ion but shows acid catalysis only at pH < 1. Reactive intermediates 1 and 2 can be intercepted by other nucleophiles, such as the azide ion (k(N3)(1) = 2.0 x 10(4) M(-1) s(-1) and k(N3)(2) = 3.0 x 10(4) M(-1) s(-1)) or thiol (k(SH)(1) = 2.2 x 10(5) M(-1) s(-1) and k(SH)(2) = 3.3 x 10(5) M(-1) s(-1)). Ethyl vinyl ether readily reacts with 1 and 2 (k(DA)(1) = 4.1 x 10(4) M(-1) s(-1) and k(DA)(2) = 6.0 x 10(4) M(-1) s(-1)) to produce Diels-Alder adducts in excellent yield. o-Naphthoquinone methides 1 and 2 were also generated by photolysis of 3-ethoxymethyl- (3b) and 1-(ethoxymethyl)-2-naphthols (4b), as well as from (2-hydroxy-3-naphthyl)methyl- (3c) and [(2-hydroxy-1-naphthyl)methyl] trimethylammonium iodides (4c). Laser flash photolysis of 3a,b and 4a,b allows the detection of short-lived (tau(25 degrees C) approximately 12 micros) precursors of naphthoquinone methides 1 and 2. On the basis of the precursor reactivity and the results of DFT calculations, 2H-naphthoxete structure was assigned to these species.

2. Macromolecular adducts of butadiene

Tretyakova NYu, Y P Lin, P B Upton, R Sangaiah, J A Swenberg Toxicology. 1996 Oct 28;113(1-3):70-6. doi: 10.1016/0300-483x(96)03429-4.

Butadiene (BD) is an important industrial chemical classified as a probable human carcinogen. Marked species differences in susceptibility to the carcinogenic effects of BD have been observed, possibly due to the differences in its metabolism. In this work, guanine and adenine adducts formed by the reactive metabolites of BD in vitro were isolated and structurally characterized by UV spectroscopy, liquid secondary ion mass spectrometry and tandem mass spectrometry, electrospray mass spectrometry and nuclear magnetic resonance spectroscopy. The adducts were prepared by reacting purine nucleobases or nucleosides with epoxybutene (EB) or diepoxybutane (DEB) followed by HPLC separation. The reaction of guanine (Gua) with EB resulted in two isomeric products, N7-(2-hydroxy-3-buten-1-yl)guanine (EB-Gua I) and N7-(1-hydroxy-3-buten-2-yl)guanine (EB-Gua II). The reaction of adenine at N3 led to the formation of N3-(2-hydroxy-3-buten-1-yl)adenine (EB-Ade I) and N3-(1-hydroxy-3-buten-2-yl) (EB-Ade II). The major guanine adduct with DEB was identified as N7-(2',3', 4'-trihydroxybutyl)guanine (DEB-Gua-I). Three products formed from the reaction of DEB with adenine at pH 7 were identified as N3, N7 and N9-(2',3',4'-trihydroxybutyl)adenines (DEB-Ade I, II and III, respectively). Our results indicate that nucleophilic nitrogens of guanine and adenine first attack one of the epoxy groups of DEB giving (2'-hydroxy-3',4'-epoxybutane-1-yl) intermediates which can be rapidly hydrolyzed to the corresponding (2',3',4'-trihydroxybutyl) adducts or form cross-links with DNA or proteins. N7 and N3 adducts of Ade and Gua are expected to undergo spontaneous depurination and repair by methylpurine glycosylase and therefore may be useful as biomarkers of exposure in urine. The preliminary data on quantification of EB-induced N-terminal valine hemoglobin adducts in red blood cells of exposed mice and rats using modified Edman degradation followed by GC-NI MS was investigated. The amount of EB-N-terminal valine adducts in mouse globin was about 3 times greater than that in rats which may be explained by higher rates of the formation and/or limited detoxification of EB in mice. Female rats and mice had greater amounts of hemoglobin adducts than males.