3,8-dioxaspiro[4.4]nonane-4,9-dione

Base Information

• Chemical Name: 3,8-dioxaspiro[4.4]nonane-4,9-dione
• CAS No.: 4372-10-5
• Molecular Formula: C7H8O4
• Molecular Weight: 0
• Hs Code.: 2932999099
• Mol file: 4372-10-5.mol

Synonyms:2,7-dioxaspiro<4.4>nonane-1,6-dione;Di-(2-hydroxyethyl)malonsaeure-dilacton;2,7-Dioxaspiro[4.4]nonane-1,6-dione;3,8-dioxaspiro[4.4]nonane-4,9-dione;2,7-Dioxa-spiro<4,4>nonandion-1,6;2,7-Dioxa-spiro[4.4]nonan-1,6-dion;

Chemical Property of 3,8-dioxaspiro[4.4]nonane-4,9-dione

Chemical Property:

• Vapor Pressure: 2.23E-08mmHg at 25°C
• Boiling Point: 452.5°C at 760 mmHg
• Flash Point: 254.1°C
• PSA: 52.60000
• Density: 1.36g/cm³
• LogP: -0.13340

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 3,8-Dioxaspiro[4.4]nonane-4,9-dione is a spirocyclic compound synthesized via the reaction of olefins with malonic acid in the presence of manganese(III) acetate. This method offers a convenient one-step route to produce such structures, which are valuable in organic synthesis. 3,8-dioxaspiro[4.4]nonane-4,9-dione features a spiro center connecting two fused lactone rings, and its formation is influenced by the substituents on the olefins, with yields varying widely (3–84%). Characterization techniques like IR, H-NMR, and HPLC confirm its structure and configuration.

Technology Process of 3,8-dioxaspiro[4.4]nonane-4,9-dione

There total 12 articles about 3,8-dioxaspiro[4.4]nonane-4,9-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

C11H18O5 → 2,7-dioxaspiro<4.4>nonane-1,6-dione (4372-10-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2019.03.074

Reference yield: 29.0%

ethene (74-85-1) + malonic acid (141-82-2) → 2,7-dioxaspiro<4.4>nonane-1,6-dione (4372-10-5)

Guidance literature:

With manganese triacetate; acetic acid; at 70 ℃; for 2h; under 760 Torr;

DOI:10.1021/jo00207a024

Reference yield:

C17H30O7 → 2,7-dioxaspiro<4.4>nonane-1,6-dione (4372-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / 1,2-dichloro-ethane / 240 h / 20 °C

2: potassium carbonate; methanol / 2 h

3: toluene-4-sulfonic acid / dichloromethane / 48 h / 20 °C

With methanol; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.tetlet.2019.03.074

upstream raw materials:

diethyl malonate

ethene

malonic acid

C₁₅H₂₆O₆

Refernces

The Reaction of Olefins with Malonic Acid in the Presence of Manganese(III) Acetate

10.1246/bcsj.56.3527

The research investigates the reaction of various olefins with malonic acid in the presence of manganese(III) acetate (MA) to synthesize substituted 2,7-dioxaspiro[4.4]nonane-1,6-diones and other related compounds. The purpose is to develop a convenient one-step synthesis method for these compounds, which have potential applications in organic chemistry. Key chemicals used include olefins such as 1,1-diphenylethene, 1,1-bis(4-methoxyphenyl)ethene, methylenecyclohexane, 2-phenylpropene, styrene, 1-octene, and cyclohexene, along with malonic acid and manganese(III) acetate. The reactions were carried out in acetic acid, and the products were characterized using techniques like IR spectroscopy, H-NMR spectroscopy, and HPLC. The study concludes that this method provides a straightforward and efficient route to synthesize the target compounds, with yields ranging from 3% to 84% depending on the specific olefin used. The configurations of the products were determined based on H-NMR spectral analyses, and the results showed that the reaction outcomes varied significantly depending on the substituents on the olefins.

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