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| dbo:abstract
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- (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)
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| dbo:alternativeName
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- 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)
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- (1R,3R)-1,2,3-Trimethylcyclopentane (en)
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- 5631 (xsd:nonNegativeInteger)
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- prolonged exposure may result in cancer or health defects (en)
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| dbp:name
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| dbp:othernames
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- 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)
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| dbp:pubchem
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| dbp:smiles
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- VCWNHOPGKQCXIQ-RNFRBKRXSA-N (en)
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| rdfs:comment
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- (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)
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- (1R,3R)-1,2,3-Trimethylcyclopentane (en)
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- (1R,3R)-1,2,3-Trimethylcyclopentane (en)
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-1,2,3-trimethylcyclopentane.png?width=300)
-1,2,3-trimethylcyclopentane.png){kind=link}