1270294-05-7 | (R)-5,7-difluorochroman-4-ol

CAS:1270294-05-7 | (R)-5,7-difluorochroman-4-ol,Description

“®-5,7-Difluorochroman-4-OL”, also known as 1,3-difluoro-2-hydroxy-4-propoxybenzene, is a chiral difluorinated hydroxybenzene derivative. It is a colorless solid with a low melting point and is soluble in organic solvents. It is an important intermediate in the synthesis of tegoprazan.

Synthesis Analysis

The synthesis of “®-5,7-Difluorochroman-4-OL” involves taking 5, 7-difluorochroman-4-one as a substrate and performing an asymmetric reduction reaction in the presence of ketoreductase, coenzyme, and a coenzyme circulating system. The ketoreductase used can be one or a combination of two or more of the short-chain dehydrogenases/reductases family (SDR), medium-chain dehydrogenases/reductase (MDR), or aldo-Keto reductase (AKR).

Molecular Structure Analysis

The molecular formula of “®-5,7-Difluorochroman-4-OL” is C9H8F2O2. Its molecular weight is 186.16. The InChI code is 1S/C9H8F2O2/c10-5-3-6(11)9-7(12)1-2-13-8(9)4-5/h3-4,7,12H,1-2H2/t7-/m1/s1.

Chemical Reactions Analysis

The key chemical reaction involved in the synthesis of “®-5,7-Difluorochroman-4-OL” is the asymmetric reduction of 5, 7-difluorochroman-4-one. This reaction is facilitated by ketoreductase, coenzyme, and a coenzyme circulating system.

Physical And Chemical Properties Analysis

“®-5,7-Difluorochroman-4-OL” has a predicted boiling point of 228.4±40.0 °C and a predicted density of 1.402±0.06 g/cm3. Its pKa is predicted to be 13.09±0.20.

Scientific Research Applications

Fluorinated Compounds in Material Science

Fluorine atoms significantly influence the properties and applications of organic molecules in material science. For instance, the introduction of fluorine atoms into organic molecules, similar to the structural motif of (R)-5,7-Difluorochroman-4-OL, can enhance the materials' resistance to solvents, thermal stability, and electrical properties. This has profound implications in developing advanced materials for electronics, such as organic semiconductors and polymers for organic solar cells. A study by Jin-liang Wang et al. (2016) highlights the synthesis of multifluorine substituted oligomers showing improved photovoltaic performances and stability, indicating the potential of fluorinated compounds in organic electronics (Wang et al., 2016).

Catalysis and Synthetic Chemistry

Fluorinated heterocycles, such as those structurally related to (R)-5,7-Difluorochroman-4-OL, play a crucial role in the pharmaceutical and agrochemical industries. The synthesis of fluorinated heterocycles through catalytic methods, as discussed in the work of Jia-Qiang Wu et al. (2017), showcases the importance of fluorinated compounds in creating bioactive molecules with enhanced properties, including stability and bioavailability (Wu et al., 2017).

Fluorinated Reagents in Organic Synthesis

The development of new fluorinated reagents for organic synthesis has been a significant area of research, given the unique reactivity and properties imparted by fluorine atoms to organic molecules. Studies on electrophilic trifluoromethylthiolating reagents by X. Shao et al. (2015) exemplify how fluorinated compounds can be utilized to introduce fluorine-containing functional groups into molecules, enhancing their chemical and metabolic stability, a concept that could be applied to (R)-5,7-Difluorochroman-4-OL derivatives (Shao et al., 2015).

Fluorine in Drug Development

The inclusion of fluorine atoms in drug molecules, as would be the case with derivatives of (R)-5,7-Difluorochroman-4-OL, can significantly affect their pharmacokinetic and pharmacodynamic properties. Fluorine can improve the bioavailability, metabolic stability, and binding affinity of pharmaceuticals. The work by Y. Zafrani et al. (2017) on difluoromethyl bioisosteres highlights the role of the difluoromethyl group as a lipophilic hydrogen bond donor, potentially offering insights into designing new drugs with enhanced properties (Zafrani et al., 2017).

Magnetic Resonance Imaging (MRI)

Fluorinated compounds are valuable in MRI as they offer high signal sensitivity and specificity with minimal biological background interference. The application of fluorinated agents in MRI, as explored by Jian-xin Yu et al. (2005), demonstrates the potential of (R)-5,7-Difluorochroman-4-OL analogs in developing novel imaging agents for non-invasive physiological and pharmacological studies (Yu et al., 2005).

Safety And Hazards

“®-5,7-Difluorochroman-4-OL” is classified under the GHS07 hazard class. The signal word for this compound is “Warning” and it has hazard statements H302, H315, H319, and H335. The precautionary statements are P261, P305+P351+P338.

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