二環性の、二環式の、二環の

WordNet

having molecules consisting of two fused rings

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/15 07:43:43」(JST)

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Decalin, also known as bicyclo[4.4.0]decane

Norbornane, also known as bicyclo[2.2.1]heptane

spiro[2.2]pentane, a spirocyclic molecule

A bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.

Fusion of the rings can occur in three ways:

Across a bond between two atoms - for example, decalin (also known as bicyclo[4.4.0]decane), has a C-C bond shared between two cyclohexane rings
Across a sequence of atoms (bridgehead) - for example, norbornane (also known as bicyclo[2.2.1]heptane), can be viewed as a pair of cyclopentane rings that share three of the five carbon atoms
At a single atom (spirocyclic, forming a spiro compound)

Singly fused rings are the most common, and spiro rings are the least common.

Bridges

A bridge is an unbranched chain of atoms or an atom or a covalent bond connecting two bridgeheads in a polycyclic compound.

The main bridge is a bridge that connects the two main bridgeheads.

A secondary bridge is any bridge not included in the main ring or the main bridge.

An independent secondary bridge links bridgeheads that are part of the main ring or main bridge.

A dependent secondary bridge links at least one bridgehead that is part of a secondary bridge.

Nomenclature

Bicyclic molecules have a strict nomenclature.^[1] On its simplest level the parent hydrocarbon is the equivalent open-carbon alkane. For bridged compounds, the prefix bicyclo is added, followed by, between brackets, separated by periods, and, in descending order, the number of carbon atoms between each of the bridgeheads. For example in bicyclo[2.2.1]heptane the carbon frame contains a total of 7 atoms, hence the parent name heptane. This molecule has three bridges having 2, 2 and 1 carbon atoms, hence the prefix bicyclo[2.2.1]. For spiro compounds, terms like spiro[2.4] are used, indicating that there are 3- and 5-membered rings (because the spiro atom itself is not counted) meeting at the spiro atom.

References

^ IUPAC nomenclature for bicyclics

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Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles.

Burgeson JR, Moore AL, Gharaibeh DN, Larson RA, Cerruti NR, Amberg SM, Hruby DE, Dai D.SourceSIGA Technologies, Inc., 4575 SW Research Way, Suite 230, Corvallis, OR 97333, United States.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2013 Feb 1;23(3):750-6. doi: 10.1016/j.bmcl.2012.11.093. Epub 2012 Dec 1.
A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. Th
PMID 23265900

Design and synthesis of tricyclic cores for kinase inhibition.

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Japanese Journal

SYNTHESIS OF BICYCLIC DIOXETANES BEARING A 4-(BENZIMIDAZOL-2-YL)-3-HYDROXYPHENYL GROUP AND THEIR BASE-INDUCED CHEMILUMINESCENT DECOMPOSITION IN AN APROTIC MEDIUM AND IN AN AQUEOUS MEDIUM

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有機合成化学協会誌 71(3), 196-206, 2013
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NAID 130003373271