1489-97-0

Basic information

• Product Name: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate
• Synonyms: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate;1,4-Dioxa-8-carboethoxyspiro[4.5]decane;1,4-Dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester;Ethyl 1,4-Dioxaspiro[4.5]decan-8-carboxylate;Ethyl 4-Oxocyclohexanecarboxylate Ethylene Ketal;1,4-dioxaspiro[4.5]decane-8-carboxylate
• CAS NO: 1489-97-0
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.25822
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1489-97-0.mol
• Article Data: 104

Chemical Properties

• Boiling Point: 293.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate(1489-97-0)
• EPA Substance Registry System: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate(1489-97-0)

Safety Data

• Hazardous Substances Data: 1489-97-0(Hazardous Substances Data)

Usage

Description

Ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate is an organic compound with a unique cyclic structure that features a dioxaspiro core and a carboxylate group. It is a versatile intermediate in the synthesis of various pharmaceutical compounds due to its chemical reactivity and structural properties.

Uses

Used in Pharmaceutical Industry:
Ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate is used as a key intermediate for the synthesis of arylcyclohexanones, which are analgesics. These compounds are effective in providing pain relief and are used to treat various conditions that cause discomfort.
Ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate is also used as a precursor in the development of metalloproteinase inhibitors. These inhibitors play a crucial role in regulating the activity of metalloproteinases, which are enzymes involved in various physiological processes, including tissue remodeling and inflammation.
Furthermore, ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate is utilized in the synthesis of benzimidazole derivatives, which serve as therapeutic TRPM8 receptor modulators. TRPM8 is a temperature-sensitive ion channel that can be targeted for the treatment of various conditions, such as chronic pain and cold hypersensitivity.
Lastly, ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate is employed in the preparation of apoptosis-inducing agents. Apoptosis, or programmed cell death, is a vital process in maintaining cellular homeostasis. Modulating apoptosis can be beneficial in treating diseases where cell survival is disrupted, such as cancer.

Upstream product

• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 107-21-1 ethylene glycol 
• 874-61-3 4-oxocyclohexanecarboxylic acid 
• 6940-58-5 pentane-1,3,5-tricarboxylic acid 
• 63579-89-5 triethyl pentane-1,3,5-tricarboxylate 
• 3289-28-9 ethyl cyclohexanecarboxylate 
• 104-15-4 toluene-4-sulfonic acid 
• 58660-59-6 Diethyl cyclohexanone-2,4-dicarboxylic ester 
• 99-96-7 4-hydroxy-benzoic acid 
• 3618-04-0 4-hydroxycyclohexyl carboxylic acid ethyl ester 
• 120-47-8 Ethyl 4-hydroxybenzoate 

Downstream Products

• 78461-64-0 ethyl 1-hydroxymethyl-4-methylenedioxy-cyclohexane-1-carboxylate 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 56868-61-2 ethyl 8-benzyl-1,4-dioxa-spiro[4,5]decane-8-carboxylate 
• 4111-01-7 4-methyl-4-vinylcyclohexan-1-one 
• 78461-66-2 ethyl 1-(hydroxymethyl)-4-oxocyclohexanecarboxylate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 155192-28-2 2,2-Diallyl-4-trimethylsilanylethynyl-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexanone 
• 155192-26-0 4-Trimethylsilanylethynyl-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexanone 
• 155192-30-6 2,2-Diallyl-4-ethynyl-4-prop-2-ynyl-cyclohexanone 
• 159329-34-7 ethyl 4-benzyloxyimino-1-bromomethylcyclohexanecarboxylate 
• 159329-35-8 ethyl 1-bromomethyl-4-ethoxycarbonylmethylenecyclohexanecarboxylate 
• 159329-33-6 ethyl 1-(bromomethyl)-4-oxocyclohexanecarboxylate 
• 147905-77-9 ethyl 1-methyl-4-oxo-1-cyclohexanecarboxylate 
• 194367-71-0 (R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one 

Relevant articles and documents

Practical Manufacture of 4-Alkyl-4-aminocyclohexylalcohols Using Ketoreductases

The diastereoselective preparation of cis- or trans-4-substituted-4-aminocyclohexyl alcohols by conventional chemical processes reported in the literature requires long synthetic sequences and is not amenable to scale-up. In the past decade, ketoreductases (KREDs) have emerged as a powerful approach for the preparation of chiral secondary alcohols from prochiral ketones. This paper describes the diastereoselective preparation at the kilo scale of cis-allyl N-(4-hydroxy-1-methyl-cyclohexyl)carbamate (6a) via ketoreductase transformation. The methodology was also applicable to a set of different analogous cyclic ketones.

Divergent Total Syntheses of Yaequinolone-Related Natural Products by Late-Stage C-H Olefination

Divergent total syntheses of 10 yaequinolone-related natural products have been achieved for the first time by late-stage C-H olefination of 3,4-dioxygenated 4-aryl-5-hydroxyquinolin-2(1H)-ones, core structures of this family of natural products. A robust synthetic methodology to construct the core structures has been established, and the C-H olefination reaction has been carried out with synthetically useful yields and high levels of site-selectivity under mild reaction conditions in the presence of a Pd/S,O-ligand catalyst.

Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.