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Identification
Molecular formula
C15H26O
CAS number
40924-84-7
IUPAC name
1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one
State
State

This compound exists as a liquid at room temperature, often noted for its stability and resistance to temperature changes due to its bicyclic structure.

Melting point (Celsius)
48.30
Melting point (Kelvin)
321.45
Boiling point (Celsius)
254.40
Boiling point (Kelvin)
527.55
General information
Molecular weight
220.37g/mol
Molar mass
220.3720g/mol
Density
0.9457g/cm3
Appearence

The compound appears as a colorless or pale yellow liquid with a characteristic odor. Due to its structural complexity, it is often used in stereochemical studies and might display different colors under UV light depending on its environment.

Comment on solubility

Solubility of 1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one

The solubility properties of 1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one are influenced by its unique bicyclic structure and the presence of bulky tert-butyl groups. Due to these structural characteristics, it exhibits distinct solubility traits:

  • Polar Solvents: This compound is generally insoluble in water, a common trait for many organic compounds with significant hydrocarbon segments.
  • Nonpolar Solvents: It demonstrates good solubility in nonpolar solvents such as hexane or toluene, where interactions with solvent molecules can promote solvation.
  • Temperature Dependence: The solubility may change with temperature, often increasing as the temperature rises due to enhanced molecular movement.

Given the compound's bulky structure, one might find that it has limited interactions with polar environments, reinforcing its preference for nonpolar media. As stated, “like dissolves like,” which implies that the solubility behavior can primarily be explained by the principle of polarity matching between solute and solvent.

In summary, while 1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one struggles with polar solubility, it thrives in nonpolar solvents, making it versatile in various organic applications.

Interesting facts

Interesting Facts about 1,5-Ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one

The compound 1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one is a fascinating example of a bicyclic ketone, known for its unique structure and potential applications. Here are some interesting points to consider:

  • Unique Structure: This compound features a bicyclic framework, specifically a bicyclo[3.1.0] system. The structural arrangement contributes to its distinctive chemical behavior.
  • Bulkiness: The presence of two tert-butyl groups significantly increases steric hindrance, influencing the reactivity and stability of the molecule.
  • Applications in Chemistry: Due to its structural properties, this compound can serve as a precursor in organic synthesis or be utilized in the study of reaction mechanisms, particularly in environments where steric effects play a crucial role.
  • Research Potential: Researchers are intrigued by compounds like this one for their utility in synthesizing complex molecules, catalysis, and material science.
  • Contributors to Flavor and Fragrance: Bicyclic ketones, in general, have been studied for their potential roles in flavor and aroma compounds, reflecting how seemingly simple molecules can impact various industries.

In summary, 1,5-ditert-butyl-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one represents an intriguing avenue for exploration within organic chemistry, blending structural integrity with practical applications. Its unique characteristics spark curiosity among chemists and open doors to new chemical inquiries.

Synonyms
19377-95-8
Bicyclo[3.1.0]hexan-2-one, 1,5-di-tert-butyl-3,3-dimethyl-
1,5-Ditert-butyl-3,3-dimethylbicyclo[3.1.0]hexan-2-one
1,5-Di-tert-butyl-3,3-dimethylbicyclo[3.1.0]hexan-2-one
Bicyclo(3.1.0)hexan-2-one, 1,5-di-tert-butyl-3,3-dimethyl-
Bicyclo[3.1.0]hexan-2-one, 1,5-bis(1,1-dimethylethyl)-3,3-dimethyl-
Bicyclo[3.1.0]hexan-2-one,1,5-bis(1,1-dimethylethyl)-3,3-dimethyl-
1,5-DI-TERT-BUTYL-3,3-DIMETHYLBICYCLO(3.1.0)HEXAN-2-ONE
BPSOBKPRRBSNAW-UHFFFAOYSA-N
DTXSID80941063
1,5-di-t-butyl-3,3-dimethylbicyclo[3.1.0]hexan-2-one
3,3-DIMETHYL-1,5-DITERT-BUTYL-BICYCLO[3.1.0]HEXAN-4-ONE
Bicyclo[3.1.0]hexan-2-one, 1,5-bis-tert.-butyl-3,3-dimethyl
1,5-bis(1,1-Dimethylethyl)-3,3-dimethyl-bicyclo[3.1.0]hexan-2-one