Dimethyl (2-oxoheptyl)phosphonate
[CAS# 36969-89-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Dimethyl (2-oxoheptyl)phosphonate
• Synonyms: 1-dimethoxyphosphorylheptan-2-one
• Molecular Formula: C₉H₁₉O₄P
• Molecular Weight: 222.22
• CAS Registry Number: 36969-89-8
• EC Number: 253-293-4
• SMILES: CCCCCC(=O)CP(=O)(OC)OC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*, 1.07 g/cm³
• Index of Refraction: 1.426, Calc.^*, 1.444
• Boiling Point: 316.0±0.0 ºC (760 mmHg), Calc.^*, 109 ºC
• Flash Point: 147.6±42.9 ºC, Calc.^*, 110 ºC

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H315-H319-H332-H335-H341-H413
• Precautionary Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

Dimethyl (2-oxoheptyl)phosphonate is an organophosphorus compound with applications in organic synthesis and medicinal chemistry. The discovery of this compound can be attributed to the growing need for versatile intermediates in the synthesis of complex molecules, particularly in the development of bioactive compounds. Phosphonates, such as dimethyl (2-oxoheptyl)phosphonate, are known for their stability and ability to participate in a wide range of chemical reactions, including the Horner-Wadsworth-Emmons (HWE) reaction, which is a popular method for creating carbon-carbon double bonds.

Dimethyl (2-oxoheptyl)phosphonate is synthesized through the reaction of dimethyl phosphite with a suitable ketone or aldehyde under basic conditions. The phosphonate group provides the compound with reactivity that is useful in various coupling reactions, where it can act as a nucleophile or be used in olefination reactions to create alkenes. The compound’s 2-oxoheptyl group offers additional functionalization potential, making it a flexible intermediate in the preparation of more complex molecules.

In applications, dimethyl (2-oxoheptyl)phosphonate is widely used in the synthesis of biologically active molecules, such as pharmaceuticals and agrochemicals. The phosphonate group’s presence can enhance the biological activity of a molecule, and its stability makes it a favorable component in drug design. The compound has also been utilized in the synthesis of natural products, where its role as a key intermediate in multi-step synthetic pathways allows for the efficient construction of complex molecular architectures.

In medicinal chemistry, compounds derived from dimethyl (2-oxoheptyl)phosphonate have shown potential in enzyme inhibition and receptor binding studies. The presence of the phosphonate group can mimic phosphate groups in biological systems, making such compounds useful in studying enzyme-substrate interactions and designing enzyme inhibitors. Additionally, the phosphonate functionality offers metabolic stability, which is an important consideration in drug development.

Overall, dimethyl (2-oxoheptyl)phosphonate serves as an important building block in organic synthesis, offering a range of reactivity options for chemists engaged in the development of new materials, pharmaceuticals, and biologically active compounds.

References

2023. Some aspects of the synthesis and modification of cross-conjugated cyclopentenone prostaglandins. Russian Chemical Bulletin.
DOI: 10.1007/s11172-023-4026-4

2015. Synthesis of (�)-15-deoxy-?12,14-prostaglandin J2 and ?12-prostaglandin J2 15-acetate methyl esters. Russian Journal of Organic Chemistry.
DOI: 10.1134/s1070428015010017

2015. Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies. Synthesis.
DOI: 10.1055/s-0035-1560344