Isoindole: Difference between revisions
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{{chembox |
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| ImageFile = Isoindol.svg |
| ImageFile = Isoindol.svg |
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| ImageSize = 150px |
| ImageSize = 150px |
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| ImageName = Skeletal formula |
| ImageName = Skeletal formula |
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| ImageFile1 = Isoindole-3D-balls.png |
| ImageFile1 = Isoindole-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
| ImageName1 = Ball-and-stick model |
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| PIN=2''H''-Isoindole<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=213 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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|IUPACName=2''H''-Isoindole |
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|OtherNames= |
|OtherNames= |
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|Section1= |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2282425 |
| ChemSpiderID = 2282425 |
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| InChI = 1/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H |
| InChI = 1/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VHMICKWLTGFITH-UHFFFAOYSA-N |
| StdInChIKey = VHMICKWLTGFITH-UHFFFAOYSA-N |
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| CASNo=270-68-8 |
| CASNo=270-68-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = PR6T8TL5NT |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 33179 |
| ChEBI = 33179 |
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|Section2= |
|Section2={{Chembox Properties |
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| Formula=C<sub>8</sub>H<sub>7</sub>N |
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| MolarMass=117.15 g/mol |
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|Section3={{Chembox Hazards |
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In [[organic chemistry]] and [[heterocyclic chemistry]], '''isoindole''' consists of a [[benzene]] ring fused with [[pyrrole]].<ref>{{ cite book | author = Gilchrist, T. L. | title = Heterocyclic Chemistry | year = 1987 | publisher = Longman | isbn = 0-582-01422-0 }}</ref> The compound is an [[isomer]] of [[indole]]. Its [[organic reduction|reduced]] form is [[isoindoline]]. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in [[phthalocyanine]]s, an important family of dyes. Some [[alkaloid]]s containing isoindole have been isolated and characterized.<ref name= Heugebaert>Heugebaert, Thomas S. A.; Roman, Bart I.; Stevens, Christian V. "Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles" Chemical Society Reviews 2012, volume 41, pp. 5626-5640. {{doi|10.1039/c2cs35093a}}</ref><ref>See for example: {{Cite journal |
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'''Isoindole''' in [[heterocyclic chemistry]] is a [[arene compound|benzo]] fused [[pyrrole]].<ref>Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01422-0</ref> The compound is an [[isomer]] of [[indole]] and its [[organic reduction|reduced]] form is an [[isoindoline]]. |
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| last1 = Zhang | first1 = X. |
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| last2 = Ye | first2 = W. |
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| last3 = Zhao | first3 = S. |
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| last4 = Che | first4 = C. T. |
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| title = Isoquinoline and isoindole alkaloids from Menispermum dauricum |
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| doi = 10.1016/j.phytochem.2003.12.004 |
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| journal = Phytochemistry |
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| volume = 65 |
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| issue = 7 |
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| pages = 929–932 |
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| year = 2004 |
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| pmid = 15081297 |
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| pmc = |
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}}</ref> |
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==Synthesis== |
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In solution its [[tautomer]] without full aromaticity over the whole ring system is predominant:{{Citation needed|date=February 2008}} |
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The parent isoindole was prepared by [[flash vacuum pyrolysis]] of an N-substituted isoindoline.<ref>R. Bonnett and R. F. C. Brown "Isoindole" J. Chem. Soc., Chem. Commun., 1972, 393-395. {{doi|10.1039/C39720000393}}</ref> N-Substituted isoindoles, which are easier to handle, can be prepared by dehydration of isoindoline-N-oxides. They also arise by myriad other methods, e.g., starting from xylylene dibromide (C<sub>6</sub>H<sub>4</sub>(CH<sub>2</sub>Br)<sub>2</sub>). |
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==Structure and tautomerism of 2-H-isoindoles == |
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: [[File:Isoindoletautomerism.png|400px|Isoindole tautomerism]] |
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Unlike indole, isoindoles exhibit noticeable alternation in the C-C bond lengths, which is consistent with their description as pyrrole derivatives fused to a butadiene. |
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In solution, the 2''H''-isoindole [[tautomer]] predominates. It resembles a [[pyrrole]] more than a simple [[imine]].<ref>{{cite book | title = Handbook of Heterocyclic Chemistry |author1=Alan R. Katritzky |author2=Christopher A. Ramsden |author3=J. Joule |author4=Viktor V. Zhdankin | page = 133 | publisher = Elsevier | year = 2010}}</ref> The degree to which the 2''H'' predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.<ref>{{cite book | title = Heterocyclic Chemistry |author1=John A. Joule |author2=Keith Mills | publisher = John Wiley & Sons | year = 2010 | page = 447}}</ref> |
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and therefore the compound resembles a [[pyrrole]] more than a simple [[imine]]. Isoindoles are building blocks for [[phthalocyanine]]s which are relevant as dyes |
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:[[File:Isoindoletautomerism.svg|thumb|left|400px|2''H''-Isoindole (right) is the predominant tautomer relative to 1''H''-isoindole (left)]]{{clear left}} |
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N-Substituted isoindoles do not engage is tautomerism and are therefore simpler to study. |
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<gallery caption="Illustrative Isoindoline Derivatives" widths="130px" heights="120px" > |
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File:PY139.svg|[[Pigment yellow 139]], a common high performance pigment. |
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File:PY185.svg|[[Pigment yellow 185]], a common high performance pigment. |
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File:Copper phthalocyanine.svg|[[Copper phthalocyanine]], one of the most pervasive synthetic pigments. |
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</gallery> |
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== See also == |
== See also == |
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* [[1,3-Disubstituted Isoindolines]]. |
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* [[Isoindene]] with nitrogen replaced by a [[methylene |
* [[Isoindene]] with nitrogen replaced by a [[methylene group. |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Simple aromatic rings}} |
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[[ar:أيزوإندول]] |
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[[Category:Simple aromatic rings]] |
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[[fr:Isoindole]] |
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[[ja:イソインドール]] |