(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
[CAS# 204254-96-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
• Synonyms: [1S-(1a,5b,6a)]-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.33
• CAS Registry Number: 204254-96-6
• EC Number: 429-020-1
• SMILES: CCC(CC)O[C@@H]1C=C(C[C@H]2[C@@H]1O2)C(=O)OCC

Safety Data

• Hazard Symbols: GHS08;GHS07 Warning
• Risk Statements: H373-H317
• Safety Statements: P260-P261-P272-P280-P302+P352-P319-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate is a complex organic compound known for its distinctive bicyclic structure and functional groups. This compound has gained attention in the fields of organic synthesis and medicinal chemistry due to its unique chemical properties and potential applications.

The discovery of (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate emerged from research into bicyclic compounds with specific stereochemical configurations. The synthesis of this compound typically involves the formation of the bicyclic structure through cyclization reactions, followed by functionalization to introduce the ethyl ester and pentan-3-yl-oxy groups. This synthetic route requires careful control of reaction conditions to achieve the desired stereochemistry and product purity.

In organic synthesis, (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate is valued for its role as an intermediate in the preparation of more complex molecules. Its unique bicyclic framework and functional groups provide a versatile platform for further chemical modifications. The compound is used in the synthesis of various bioactive molecules and pharmaceuticals, where its structure can be modified to introduce additional functional groups or to create novel compounds with specific biological activities.

In medicinal chemistry, the compound has shown promise as a lead structure for the development of new drugs. Its bicyclic structure is of interest for designing molecules that can interact with biological targets in unique ways. The presence of the ethyl ester and pentan-3-yl-oxy groups enhances its potential as a drug candidate by influencing its pharmacokinetic properties, such as solubility and stability. Research into its biological activity has revealed potential applications in treating diseases where novel drug interactions are required.

Additionally, (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate finds applications in materials science. Its bicyclic structure and functional groups make it useful for developing materials with specific chemical properties, such as enhanced mechanical strength or unique reactivity. The compound can be incorporated into polymer matrices or used as a building block for creating advanced materials with tailored characteristics.

Overall, (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate is a significant compound in organic synthesis and medicinal chemistry. Its unique structure and versatile functionality make it a valuable intermediate for further chemical research and development, with potential applications spanning from drug discovery to materials science.

References

1999. Industrial Synthesis of the Key Precursor in the Synthesis of the Anti-Influenza Drug Oseltamivir Phosphate (Ro 64-0796/002, GS-4104-02): Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate. Organic Process Research & Development, 3(4).
DOI: 10.1021/op9900176