27513-35-5

Basic information

• Product Name: Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester
• Synonyms: Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester;3,5-Dioxocyclohexanecarboxylic Acid Ethyl Ester;Ethyl 3,5-dioxocyclohexanecarboxylate
• CAS NO: 27513-35-5
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.18918
• Product Categories: Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 27513-35-5.mol

Chemical Properties

• Boiling Point: 125-126 °C(Press: 0.4 Torr)
• Appearance: /
• Density: 1.199±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Soluble), Dichloromethane (Slightly), Dimethylformamide (Slightly),
• PKA: 4.42±0.20(Predicted)
• CAS DataBase Reference: Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester(27513-35-5)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester(27513-35-5)

Safety Data

• Hazardous Substances Data: 27513-35-5(Hazardous Substances Data)

Usage

Uses

1. Plant Growth Retardants:
Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester is used as a reactant in the preparation of plant growth retardants. These retardants are essential in controlling the growth of plants, particularly in agriculture, to prevent excessive growth and improve crop yield.
2. Cyclopropanecarbonyloxy Cyclohexenone Derivatives:
Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester is also utilized in the synthesis of cyclopropanecarbonyloxy cyclohexenone derivatives. These derivatives act as hydroxyphenylpyruvate dioxygenase inhibitors, which are crucial in various chemical and pharmaceutical applications.
3. Pharmaceutical Industry:
In the pharmaceutical industry, Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester is used as a reactant for the development of new drugs and therapeutic agents. Its unique chemical properties make it a valuable component in the synthesis of various pharmaceutical compounds.
4. Chemical Synthesis:
Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester is employed in chemical synthesis, particularly in the production of various organic compounds and intermediates. Its versatility as a reactant allows for the creation of a wide range of products with diverse applications.

Upstream product

• 1187-74-2 diethyl 2-acetylmethyl-1,4-butanedioate 
• 1520-50-9 but-2-enedioic acid diethyl ester 
• 141-05-9 Diethyl maleate 
• 17596-10-0 diethyl 2-ethoxysuccinate 

Downstream Products

• 199446-36-1 3-cyclopropanecarbonyloxy-5-ethoxycarbonyl-2-cyclohexen-1-one 
• 85894-65-1 3-Acetoxy-5-oxo-cyclohex-3-enecarboxylic acid ethyl ester 

Relevant articles and documents

BICYCLIC IMIDAZOLE DERIVATIES USEFUL FOR THE TREATMENT OF RENAL DISEASE, CARDIOVASCULAR DISEASES AND FIBROTIC DISORDERS

The present invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5 and n are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

A trinexapac-and intermediate preparation method

The invention discloses a preparation method of trinexapac-ethyl and an intermediate thereof. The method comprises the following steps: under the action of an alkali, reacting acetoacetic ester (I) with diethyl maleate to obtain an intermediate (II), cont

Method for synthesizing prohexadione calcium and trinexapac-ethyl

The invention discloses a method for synthesizing prohexadione calcium and trinexapac-ethyl. The method comprises the following steps: reacting diethyl maleate (alpha, beta unsaturated carboxylic acid) with sodium ethoxide to obtain high-purity intermediate compound as shown in a formula II, and preparing prohexadione calcium and trinexapac-ethyl from the compound as shown in the formula II. In the reacting steps for preparing the compound as shown in the formula II, sodium ethoxide serving as a reactant participates in the reaction rather than a strong basic catalyst; a 1,3-cyclohexanedione compound is prepared from the intermediate compound as shown in the formula II and acetone under a reflux condition, and the total yield for the reaction of two steps can be 87 percent. The method has the advantages of low energy consumption, short reaction time, easy operation and the like by using the 1,3-cyclohexanedione compound as the intermediate, and can be used for preparing prohexadione calcium and trinexapac-ethyl with high yield.

SAR studies of 3-cyclopropanecarbonyloxy-2-cyclohexen-1-one as inhibitors of 4-hydroxyphenylpyruvate dioxygenase

Various 3-cyclopropanecarbonyloxy-2-cyclohexen-1-one 1 derivatives have been synthesized and tested as inhibitors of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) from pig liver. The inhibition results indicated that well-positioned dicarbonyl groups as well as the cyclopropyl group of 1 were essential for potent inhibition. Substitution at the 2-position of the ring system has a significant effect on inhibitor potency, while the 5-position can undergo substantial variations and retain inhibitor potency. In the compounds examined, 2-chloro substituted 12 is the best inhibitor of all with IC50 of 15 nM, the rest of the synthesized analogues were less potent inhibitors than the parent compound.