(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
[CAS# 110351-94-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
• Synonyms: Exatecan Intermediate 1
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• CAS Registry Number: 110351-94-5
• EC Number: 828-521-6
• SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CCC(=O)C3=C2)O

Properties

• Solubility: Freely soluble (371 g/L) (25 °C), Calc.^*
• Density: 1.50±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 183-185 °C (decomp)^**
• Boiling point: 656.5±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 350.9±31.5 °C (Calc.)^*
• Index of refraction: 1.623 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Kuang, Yun-Yan

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a complex organic compound that belongs to the class of heterocyclic compounds. Its molecular structure consists of a fused polycyclic framework, including an indolizine ring system fused with a pyran ring. The molecule also contains hydroxyl, ethyl, and carbonyl functional groups, which contribute to its chemical reactivity and potential applications.

The synthesis of this compound likely involves a series of multi-step organic reactions. The synthesis process would begin with a suitable precursor, such as a substituted indolizine derivative, which undergoes reactions like cyclization, functional group transformations, and ring-fusion reactions to form the fused structure seen in this compound. Specific synthetic strategies might include electrophilic aromatic substitution, nucleophilic addition reactions, and oxidative processes to introduce the necessary functional groups, such as the ethyl group, hydroxyl group, and carbonyl groups.

The stereochemical designation "(4S)" indicates that the compound has a specific configuration at the 4-position of the molecule, which could influence the compound's biological activity and chemical reactivity. Stereochemistry plays an important role in the biological activities of molecules, as it can affect interactions with biological targets, such as enzymes, receptors, or other biomolecules.

This compound, due to its heterocyclic nature and functional groups, may exhibit a wide range of potential biological activities. Indolizine derivatives have been studied for their diverse pharmacological properties, including antimicrobial, antitumor, and anti-inflammatory effects. The presence of the pyran ring and the trione functionality, which contains three carbonyl groups, may contribute to further chemical reactivity, possibly influencing its interaction with metal ions or other substrates in chemical and biological contexts.

One potential application of (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione could be in the design of novel therapeutic agents. Its unique structural features, including the fused heterocyclic rings and hydroxyl and carbonyl functionalities, might allow it to act as an enzyme inhibitor or as a ligand in medicinal chemistry. Additionally, its polycyclic structure may provide stability and enhance its ability to interact with specific biological targets, making it a candidate for further exploration in drug discovery.

Furthermore, the compound's unique structure could also lend itself to potential use in materials science, particularly in the development of organic semiconductors or optoelectronic materials. The conjugated system provided by the polycyclic ring structure may give rise to electronic properties that could be utilized in organic electronics, such as organic light-emitting diodes (OLEDs) or organic solar cells.

In conclusion, (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a complex and potentially bioactive organic compound with a unique polycyclic structure. The functional groups present, along with its stereochemistry, suggest that this compound may be useful for various applications in medicinal chemistry and materials science. Further research into its synthesis, reactivity, and biological properties could reveal new potential uses for this compound in drug development and organic electronics.