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create by mixing or combining
(chemistry) a substance formed by chemical union of two or more elements or ingredients in definite proportion by weight (同)chemical_compound
put or add together; "combine resources" (同)combine
an enclosure of residences and other building (especially in the Orient)
a whole formed by a union of two or more elements or parts
combine so as to form a whole; mix; "compound the ingredients" (同)combine
calculate principal and interest
composed of more than one part; "compound leaves are composed of several lobes; "compound flower heads"
consisting of two or more substances or ingredients or elements or parts; "soap is a compound substance"; "housetop is a compound word"; "a blackberry is a compound fruit"
combined into or constituting a chemical compound

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(…になるように)〈要素・成分など〉'を'混ぜ合わせる《+『名』+『into』+『名』》;(…から)〈薬など〉'を'調合する,混ぜ合わせて作る《+『名』+『from』(『of』)+『名』》 / 《しばしば受動態で》〈めんどうな事・損害など〉'を'もっとひどくする / 〈利子〉'を'複利で計算する / (…と)話し合いをつける,妥協する《+『with』+『名』》 / 複合の,合成の / 『合成物』,混合物,調合物;化合物 / 複合語,合成語(classroom, heart-to-heartなどをいう)
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/10 23:23:22」(JST)

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Erythromycin is an example of a naturally occurring macrocycle of medicinal significance.

A macrocycle is, as defined by IUPAC, "a cyclic macromolecule or a macromolecular cyclic portion of a molecule".^[1] In the chemical literature, macrocycles varyingly include molecules containing rings of 8 or more atoms,^[2]^[3] or 12 or more atoms.^[4] Well-known examples are the group of drugs known as macrolides. The IUPAC definition notes that a "cyclic macromolecule has no end-groups but may nevertheless be regarded as a chain", and that "macrocycle is sometimes used [in the literature] for molecules of low relative molecular mass that are not considered macromolecules.^[5] Many macrocycles are employed as macrocyclic ligands.

Synthesis

In general, macrocycles are synthesized from smaller, usually linear, molecules.

There are two major categories for synthesizing macrocycles, priority in both being to maximize yields of the required product by choosing strategies which inhibit competing linear polymerization and other reactions.^[6]

Direct synthesis

This cyclization proceeds by a conventional organic reaction, not requiring any kind of directional influence of a metal ion. Usually involves equimolar concentration of the reagents in order to produce a 1:1 condensation reaction, either at high-dilution conditions or moderate to low dilution conditions.

Template synthesis

Some cyclizations are facilitated by the presence of metal ions, which helps organize the formation of the macrocyclic ligand. The metal ion acts as a 'template' for the cyclization reaction. Phthalocyanine was the first synthetic macrocycle produced by template reaction. The metal ion may direct the condensation preferentially to cyclic rather than polymeric products (the kinetic template effect) or stabilize the macrocycle once formed (the thermodynamic template effect).

18-Crown-6 is a macrocyclic ligand produced by a template reaction using potassium ion as the templating cation.

Related molecular categories

Cryptand: a macrocycle with multiple loops (e.g., bicyclic).
Rotaxane: macrocycle(s) stuck on a stick, generally freely
Catenane: interlocked molecular rings (like a chain).
Molecular knot: a molecule in the shape of a knot such as a trefoil knot.

References

^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "macrocycle".
^ Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996.
^ J. D. Dunitz. Perspectives in Structural Chemistry (Edited by J. D. Dunitz and J. A. Ibers), Vol. 2, pp. l-70; Wiley, New York (1968)
^ Parker, S.P. (2002). McGraw-Hill Science & Technology Dictionary. McGraw-Hill. ISBN 978-0070423138. ^{[page needed]}
^ "Glossary of basic terms in polymer science (IUPAC Recommendations 1996)" (PDF). Pure and Applied Chemistry. 68 (12): 2287–2311. 1996. doi:10.1351/pac199668122287.
^ L.F Lindloy, The Chemistry of Macrocylic Ligand Complexes, Cambridge University Press, 1989, 20-50 ISBN 0-521-25261-X

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Japanese Journal

Cramping an Alkyl Group by Rigid Macrocyclic Framework

Toyota Shinji,Oki Tomohiro,Inoue Masataka,Wakamatsu Kan,Iwanaga Tetsuo
Chemistry Letters 44(7), 978-980, 2015
… An anthracene–acetylene cyclic dimer with an intra-annular ethyl group was synthesized as a sterically congested π-conjugated compound by cyclization with Sonogashira coupling. … The ethyl group was conformationally cramped by the rigid macrocyclic framework because of the severe steric interactions, as revealed by 1H NMR spectroscopy and DFT calculation. …
NAID 130005085173

A Macrocyclic Phenanthroline–Copper Complex with Less Steric Hindrance: Synthesis, Structure, and Application to the Synthesis of a [2]Rotaxane

Saito Shinichi,Ohkubo Takanori,Yamazaki Yukari,Yokoyama Tatsuyuki,Mutoh Yuichiro,Yamasaki Ryu,Kasama Takeshi
Bulletin of the Chemical Society of Japan advpub(0), 2015
… We synthesized a macrocyclic 2,9-dialkyl-1,10-phenanthroline–Cu complex (9) from 1,10-phenanthroline. … Compound 9 existed as a dinuclear complex in solid state. … In solution, however, the compound existed as a mononuclear complex. … Compound 9 mediated the Glaser reaction of an alkyne with a bulky blocking group and the formation of a [2]rotaxane was observed. …
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Cramping an alkyl group by rigid macrocyclic framework

Toyota Shinji,Oki Tomohiro,Inoue Masataka,Wakamatsu Kan,Iwanaga Tetsuo
Chemistry Letters advpub(0), 2015
… An anthracene–acetylene cyclic dimer with an intraannular ethyl group was synthesized as a sterically congested π-conjugated compound by cyclization with Sonogashira coupling. … The ethyl group was conformationally cramped by the rigid macrocyclic framework because of the severe steric interactions, as revealed by 1H NMR spectroscopy and DFT calculation. …
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