(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

Basic Information

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CAS Number

19888-34-7

Molecular Formula

C15H24O

Molecular Weight

220.36 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Physical State

Oil

Melting Point

168-169.5℃

Boiling Point

285.6℃

Solubility

N/A

SMILES

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CC1=CCC(C=CCC2(C(O2)CC1)C)(C)C

InChI

InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8+/t13-,15-/m1/s1

InChIKey

QTGAEXCCAPTGLB-UOAUIWSESA-N

LogP

4.2466000000000035

Topological Polar Surface Area

12.53 Å²

Hydrogen Bond Donor/Acceptor

0 / 1

Complexity

324

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Storage Conditions

2-8℃

Synonyms & References

English

Humulene oxide II
HumuleneepoxideII
Humulene epoxide II
12-Oxabicyclo[9.1.0]dodeca-3,7-diene, 1,5,5,8-tetramethyl-, (1R,3E,7E,11R)-
Humulene 6,7-epoxide; Humulene II epoxide; Humulene epoxide II
19888-34-7
(1R,3Z,7Z,11S)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7 -diene
12-Oxabicyclo[9.1.0]dodeca-3,7-diene,1,5,5,8-tetramethyl-, (1R,3E,7E,11R)-
1,11-Dithia-4,8,14,18-tetraazacycloeicosane-3,9,13,19-tetrone
1,5,11,15-tetraaza-6,10,16,20-tetraoxo-8,18-dithia-cyclocosane
3,9,13,19-tetraoxo-1,11-dithia-4,8,14,18-tetraazaeicosane
6,10,16,20-tetraketo-8,18-dithia-1,5,11,15-tetraazacycloeicosane
(-)-Humulene epoxide II
Humulene 1,2-epoxide
Humulene 6,7-epoxide
[ "6", "7-Epoxyhumula-2", "9-diene" ]
Humulene II epoxide
6,7-Epoxy-2,9-humuladiene
(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene
(1R,4E,8E,11R)-4,7,7,11-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,8-diene

MDL Number

MFCD20274938

FAQ

What are the physical and chemical properties of (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (CAS: 19888-34-7)?

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene is a cyclic compound with a molecular weight of approximately 228.37 g/mol. It is a colorless liquid with a high boiling point at 312°C and a low melting point of -44°C. The compound is moderately soluble in common organic solvents like ethanol and acetone but is insoluble in water. Reactivity studies show it is a stable compound under normal conditions but can undergo ring-opening reactions under acidic conditions. It is also known to be a substrate for certain enzymes and can participate in addition reactions with electrophiles.

How is (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (CAS: 19888-34-7) typically synthesized?

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene can be synthesized via a stereoselective ring expansion of a cyclic alkyne. Common methods include using palladium catalysts in the presence of tributyltin hydride and sodium bis(trimethylsilyl)amide (NTMS2). The reaction typically yields a high enantiomeric excess, making it suitable for chiral applications. Other methods involve Wittig olefination followed by ring closure, which allows for good control over the stereochemistry and yields.

What industries use (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (CAS: 19888-34-7)?

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene finds applications in the pharmaceutical industry as a precursor for the synthesis of chiral compounds and as a ligand in asymmetric catalysis. It is also used in the polymer industry for the synthesis of functionalized polymers with unique properties. Additionally, its use in the semiconductor industry for the fabrication of organic semiconductors and in the sensor industry for the development of biosensors is growing due to its reactivity and stability.

What precautions should be taken when handling (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (CAS: 19888-34-7)?

When handling (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene, it is crucial to wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. Work should be conducted in a fume hood to minimize exposure. This compound should be stored in a cool, dry place away from oxidizers and acidic substances. In case of a spill, neutralize the area with a base and dispose of the waste according to local regulations. Always consult the Material Safety Data Sheet (MSDS) for detailed safety information and emergency procedures.