(1R,3R)-1,2,3-Trimethylcyclopentane (original) (raw)
(1R,3R)-1,2,3-Trimethylcyclopentane is an organic hydrocarbon alicyclic cycloalkane compound with the molecular formula C8H16. It is a saturated cyclopentane with three methyl substituents branching off carbons 1,2, and 3. The methyl groups off carbons 1 and 3 are trans with respect to each other, while the methyl group off carbon 2 has undefined stereochemistry, allowing it to be either cis or trans with respect to methyl 1 or 3.
-1,2,3-trimethylcyclopentane.png?width=300)
| Property | Value |
|---|---|
| dbo:ChemicalSubstance/boilingPoint | 389.45 |
| dbo:ChemicalSubstance/density | 755.0 |
| dbo:abstract | (1R,3R)-1,2,3-Trimethylcyclopentane is an organic hydrocarbon alicyclic cycloalkane compound with the molecular formula C8H16. It is a saturated cyclopentane with three methyl substituents branching off carbons 1,2, and 3. The methyl groups off carbons 1 and 3 are trans with respect to each other, while the methyl group off carbon 2 has undefined stereochemistry, allowing it to be either cis or trans with respect to methyl 1 or 3. Each carbon atom within the cyclopentane ring is sp3 hybridized with the theoretical C-C-C bond angles near 108 degrees. Therefore ring strain is less prominent compared to other cycloalkanes as there is minimal deviation from the ideal tetrahedral bond angle, 109.5 degrees. However, in a planar molecule such as (1R,3R)-1,2,3-trimethylcyclopentane eclipsing interactions of adjacent C-H, adjacent methyl groups, and adjacent methyl groups & C-H bonds can contribute considerable strain. Therefore, the ring distorts slightly to adopt a minimum energy conformation that reduces the unfavorable eclipsing interactions. There are two puckered conformations exist for five-member ring systems. Such conformations include the envelope (IHIPOE, ACUHUB) and the half-chair (LISLOO, ABIKUR); please refer to figure at right. Little energy differences exist between each conformation, and it is not uncommon for five-membered ring systems such as (1R,3R)-1,2,3-trimethylcyclopentane to adopt a moderate conformation that lies somewhere between the two. (en) |
| dbo:alternativeName | Cyclopentane, 1,2,3-trimethyl-, cis-1,2,trans-1,3- (en) cis-1,2-trans-3-Trimethylcyclopentane (en) Cyclopentane,1,2,3-trimethyl-, (1a,2a,3b)- (en) |
| dbo:boilingPoint | 389.450000 (xsd:double) |
| dbo:casNumber | 15890-40-1 |
| dbo:chemSpiderId | 25623 |
| dbo:density | 755.000000 (xsd:double) |
| dbo:iupacName | (1R,3R)-1,2,3-Trimethylcyclopentane (en) |
| dbo:pubchem | 27533 |
| dbo:smiles | C[C@@H]1CC[C@H](C1C)C |
| dbo:thumbnail | wiki-commons:Special:FilePath/(1R,3R)-1,2,3-trimethylcyclopentane.png?width=300 |
| dbo:wikiPageID | 37376135 (xsd:integer) |
| dbo:wikiPageLength | 5631 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1086002137 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Cancer dbr:Alicyclic_compound dbr:Hydrocarbon dbr:Respiratory_system dbr:Cycloalkane dbr:United_States_Environmental_Protection_Agency dbc:Cyclopentanes dbr:Orbital_hybridisation dbr:Organic_chemistry dbr:Circulatory_system dbr:Gasoline dbr:Liver dbr:Stereoisomer dbr:Liquefied_petroleum_gas dbr:Kidney dbr:Methyl_group dbr:Neurology dbr:Immune_system dbr:Reproductive_system dbr:Ring_strain |
| dbp:boilingptNotes | at 760 mmHg (en) |
| dbp:boilingptc | 116.300000 (xsd:double) |
| dbp:c | 8 (xsd:integer) |
| dbp:casno | 15890 (xsd:integer) |
| dbp:chemspiderid | 25623 (xsd:integer) |
| dbp:density | 0.755 |
| dbp:flashptc | 9.200000 (xsd:double) |
| dbp:h | 16 (xsd:integer) |
| dbp:imagefile | -123 (xsd:integer) |
| dbp:imagesize | 200 (xsd:integer) |
| dbp:iupacname | -123 (xsd:integer) |
| dbp:mainhazards | prolonged exposure may result in cancer or health defects (en) |
| dbp:name | -123 (xsd:integer) |
| dbp:othernames | Cyclopentane, 1,2,3-trimethyl-, cis-1,2,trans-1,3- (en) Cyclopentane,1,2,3-trimethyl-, - (en) cis-1,2-trans-3-Trimethylcyclopentane (en) |
| dbp:pubchem | 27533 (xsd:integer) |
| dbp:smiles | C[C@@H]1CC[C@H]C (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | VCWNHOPGKQCXIQ-RNFRBKRXSA-N (en) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Reflist |
| dcterms:subject | dbc:Cyclopentanes |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 dbo:ChemicalCompound |
| rdfs:comment | (1R,3R)-1,2,3-Trimethylcyclopentane is an organic hydrocarbon alicyclic cycloalkane compound with the molecular formula C8H16. It is a saturated cyclopentane with three methyl substituents branching off carbons 1,2, and 3. The methyl groups off carbons 1 and 3 are trans with respect to each other, while the methyl group off carbon 2 has undefined stereochemistry, allowing it to be either cis or trans with respect to methyl 1 or 3. (en) |
| rdfs:label | (1R,3R)-1,2,3-Trimethylcyclopentane (en) |
| owl:sameAs | wikidata:(1R,3R)-1,2,3-Trimethylcyclopentane https://global.dbpedia.org/id/GAaiu |
| prov:wasDerivedFrom | wikipedia-en:(1R,3R)-1,2,3-Trimethylcyclopentane?oldid=1086002137&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/(1R,3R)-1,2,3-trimethylcyclopentane.png |
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| foaf:name | (1R,3R)-1,2,3-Trimethylcyclopentane (en) |
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| is dbo:wikiPageWikiLink of | dbr:(1R,3R)-1,2,3-trimethylcyclopentane dbr:Glossary_of_chemical_formulae |
| is foaf:primaryTopic of | wikipedia-en:(1R,3R)-1,2,3-Trimethylcyclopentane |
