Twistane

Names

IUPAC name

tricyclo[4.4.0.0^3,8]decane

Identifiers

CAS Number

253-14-5^Y
37165-28-8 (−)^N
21449-14-9 (+)^N

3D model (JSmol)

Interactive image

InChI

InChI=1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2

SMILES

C1CC2CC3CCC2CC13

Properties

Chemical formula

C₁₀H₁₆

Molar mass

136.24 g·mol⁻¹

Melting point

163 to 164.8 °C (325.4 to 328.6 °F; 436.1 to 437.9 K)

Structure

Coordination geometry

D₂

Dipole moment

0 D

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Twistane (IUPAC name: tricyclo[4.4.0.0^3,8]decane) is an organic compound with the formula C₁₀H₁₆. It is a cycloalkane and an isomer of the simplest diamondoid, adamantane, and like adamantane, is not very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat". The compound was first reported by Whitlock in 1962.

Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclo[2.2.2]octane framework. A 1967 publication concerned a intramolecular aldol condensation of a cis-decalin diketone. It is formed when basketane is hydrogenated.

The only symmetry operation in twistane is rotation, and there exists three 2-fold axes as shown in the left picture. Thus the point group of twistane is D₂. Although twistane has four stereocenters, it only exists as two enantiomers. This is because it is symmetric along its C₂ axis.

Polytwistane is a hypothetical polymer of fused twistane units awaiting actual synthesis.

...
Wikipedia