regioselective

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regioselectively、regioselectivity

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/08/03 01:06:31」(JST)

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In chemistry, regioselectivity is the preference of one direction of chemical bond making or breaking over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will add.

A specific example is a halohydrin formation reaction with 2-propenylbenzene:

Because of the preference for the formation of one product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other.

Certain examples of regioselectivity have been formulated as rules for certain classes of compounds under certain conditions, many of which are named. Among the first introduced to chemistry students are Markovnikov's rule for the addition of protic acids to alkenes, and the Fürst-Plattner rule for the addition of nucleophiles to derivatives of cyclohexene, especially epoxide derivatives.

Regioselectivity in ring-closure reactions is subject to Baldwin's rules. If there are two or more orientations that can be generated during a reaction, one of them is dominant (e.g., Markovnikov/anti-Markovnikov addition across a double bond)

Regioselectivity can also be applied to specific reactions such as addition to pi ligands.

See also

Finally, the selectivity often seen in carbene insertions or Baeyer-Villiger insertions of oxygen are regioselective, not chemoselective. Baeyer-Villiger reactions, which can be both chemical or biotransformations, exhibit selectivity because the oxygen inserts between the carbonyl and the more highly substituted carbon. In a study involving acetophenones, the oxygen preferentially inserts between the carbonyl and the aryl group to give acetic acid aryl esters, not methyl benzoates. Like the Markovnikov additions, the product depends on the stability of the intermediate compounds.

• Cryptoregiochemistry
• Chemoselectivity
• Stereoselectivity

References

English Journal

• Hydrotalcite catalysis for the synthesis of new chiral building blocks.

• Rodilla JM1, Neves PP1, Pombal S1, Rives V2, Trujillano R2, Díez D3.
• Natural product research.Nat Prod Res.2016 Apr;30(7):834-40. doi: 10.1080/14786419.2015.1075525. Epub 2015 Oct 9.
• The use of hydrotalcites for the synthesis of two chiral building blocks in a simple way is described as a new and green methodology. The synthesis of these compounds implies a regioselective Baeyer-Villiger reaction in a very selective way with ulterior opening and lactonisation. This methodology s
• PMID 26453245

• Effective enzymatic caffeoylation of natural glucopyranosides.

• Chyba A1, Mastihuba V1, Mastihubová M2.
• Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2016 Mar 15;26(6):1567-70. doi: 10.1016/j.bmcl.2016.02.010. Epub 2016 Feb 4.
• Reaction system was developed for enzymatic caffeoylation of model saccharidic acceptor methyl β-d-glucopyranoside to obtain exclusively methyl 6-O-caffeoyl-β-d-glucopyranoside. Reaction with starting concentration of acceptor 0.2M provided 73% yield of purified product within 17days. Reactions wi
• PMID 26896186

• Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B.

• Fobofou SA1, Franke K1, Porzel A1, Brandt W1, Wessjohann LA1.
• Journal of natural products.J Nat Prod.2016 Mar 7. [Epub ahead of print]
• The chemical investigation of the chloroform extract of Hypericum lanceolatum guided by 1H NMR, ESIMS, and TLC profiles led to the isolation of 11 new tricyclic acylphloroglucinol derivatives, named selancins A-I (1-9) and hyperselancins A and B (10 and 11), along with the known compound 3-O-geranyl
• PMID 26950610

Japanese Journal

• REGIOSELECTIVE SYNTHESIS OF PYRAZOLES AND PYRAZOLO[1,5-α]PYRIMIDINES : STRUCTURAL CHARACTERIZATION BY HMBC NMR

• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(9), 1781-1796, 2015-09-01
• NAID 40020609157

• ORGANOCATALYTIC REGIOSELECTIVE THREE-COMPONENT, ONE-POT ALLYLIC SUBSTITUTION OF MORITA-BAYLIS-HILLMAN CARBONATES

• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(5), 1028-1035, 2015-05-01
• NAID 40020460077

• A SYNTHESIS OF LAMELLARINS VIA REGIOSELECTIVE ASSEMBLY OF 1,2,3-DIFFERENTIALLY SUBSTITUTED 5,6-DIHYDROPYRROLO[2,1-a]ISOQUINOLINE CORE

• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(4), 782-794, 2015-04-01
• NAID 120005603846

Related Links

• regioselectiveの意味・用例｜英辞郎 on the WEB：アルク

regioselective 【形】《化》位置選択的な - アルクがお届けする進化するオンライン英和・和英辞書データベース。一般的な単語や連語から、イディオム、専門用語、スラングまで幅広く収録。

• Regioselective | Fundstellen im Internet | cyclopaedia.net

Fundstellen zu "Regioselective" im Internet, an Universitäten und in der Literatur... cyclopaedia.net ... http://pubs.acs.org/doi/full/10.1021/ja3058138 Lei Jiao, Eberhardt Herdtweck, and Thorsten Bach Journal of the American Chemical ...

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regioselectivity、regioselective

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位置選択的

「位置選択的」

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英

regioselective、regioselectively

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位置選択性

「regioselectivity」

　　[★]

• 位置選択性

関

regioselective

「regioselectively」

　　[★]

• 位置選択的に

関

regioselective