Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 15:13, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit		Latest revision as of 16:21, 27 November 2022 edit undoCrafterNova (talk | contribs)Extended confirmed users16,640 edits +wording +linksTags: Mobile edit Mobile web edit Advanced mobile edit
(29 intermediate revisions by 26 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
	| verifiedrevid = 443883679		| verifiedrevid = 443885075
	| ImageFile = Isoindol.svg		| ImageFile = Isoindol.svg
	| ImageSize = 150px		| ImageSize = 150px
	| ImageName = Skeletal formula		| ImageName = Skeletal formula
	| ImageFile1 = Isoindole-3D-balls.png		| ImageFile1 = Isoindole-3D-balls-2.png
	| ImageName1 = Ball-and-stick model		| ImageName1 = Ball-and-stick model
			| PIN=2''H''-Isoindole<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=213 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
	|IUPACName=2''H''-Isoindole
	|OtherNames=		| OtherNames=
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 2282425		| ChemSpiderID = 2282425
	| 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
Line 17:		Line 17:
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = VHMICKWLTGFITH-UHFFFAOYSA-N		| StdInChIKey = VHMICKWLTGFITH-UHFFFAOYSA-N
		⚫	| CASNo_Ref = {{cascite|correct|??}}
	| CASNo=270-68-8		| CASNo=270-68-8
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem=3013853
			| UNII = PR6T8TL5NT
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| PubChem=3013853
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 33179		| ChEBI = 33179
	| SMILES = c1cccc2c1cnc2		| SMILES = c1cccc2c1cc2
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>8</sub>H<sub>7</sub>N		| Formula=C<sub>8</sub>H<sub>7</sub>N
	| MolarMass=117.15 g/mol		| MolarMass=117.15 g/mol
	| Appearance=		| Appearance=
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=
	| BoilingPt=		| BoilingPt=
	| Solubility=		| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			In ] and ], '''isoindole''' consists of a ] ring fused with ].<ref>{{ cite book | author = Gilchrist, T. L. | title = Heterocyclic Chemistry | year = 1987 | publisher = Longman | isbn = 0-582-01422-0 }}</ref> The compound is an ] of ]. Its ] form is ]. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in ]s, an important family of dyes. Some ]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
	'''Isoindole''' in ] is a ] fused ].<ref>Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01422-0</ref> The compound is an ] of ] and its ] form is an ].
			| last1 = Zhang | first1 = X.
			| last2 = Ye | first2 = W.
			| last3 = Zhao | first3 = S.
			| last4 = Che | first4 = C. T.
			| title = Isoquinoline and isoindole alkaloids from Menispermum dauricum
			| doi = 10.1016/j.phytochem.2003.12.004
			| journal = Phytochemistry
			| volume = 65
			| issue = 7
			| pages = 929–932
			| year = 2004
			| pmid = 15081297
			| pmc =
			}}</ref>
			==Synthesis==
	In solution its ] without full aromaticity over the whole ring system is predominant:{{Citation needed|date=February 2008}}
			The parent isoindole was prepared by ] 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>).
			==Structure and tautomerism of 2-H-isoindoles ==
	: ]
			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.
			In solution, the 2''H''-isoindole ] predominates. It resembles a ] more than a simple ].<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>
	and therefore the compound resembles a ] more than a simple ]. Isoindoles are building blocks for ]s which are relevant as dyes
			:]{{clear left}}
⚫	== Isoindole-1,3-diones ==
			N-Substituted isoindoles do not engage is tautomerism and are therefore simpler to study.
⚫	The commercially important ] is an '''isoindole-1,3-dione''' with two ] groups attached to the heterocyclic ring. ] is an infamous drug based on this framework.
		⚫	== Isoindole-1,3-diones and related derivatives==
		⚫	The commercially important ] is an ''isoindole-1,3-dione'' with two ] groups attached to the heterocyclic ring.
			<gallery caption="Illustrative Isoindoline Derivatives" widths="130px" heights="120px" >
			File:PY139.svg|], a common high performance pigment.
			File:PY185.svg|], a common high performance pigment.
			File:Copper phthalocyanine.svg|], one of the most pervasive synthetic pigments.
			</gallery>
	== See also ==		== See also ==
			* ].
	* ] with nitrogen replaced by a ] group.		* ] with nitrogen replaced by a ].
	== References ==		== References ==
	{{reflist}}		{{reflist}}
			{{Simple aromatic rings}}
⚫	]
		⚫	]
	]
			]
	]
	]