108993-84-6

Basic information

• Product Name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylate
• Synonyms: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylate
• CAS NO: 108993-84-6
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• Mol File: 108993-84-6.mol

Chemical Properties

• Melting Point: 88-90 °C
• Boiling Point: 365.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.193±0.06 g/cm3(Predicted)
• CAS DataBase Reference: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylate(108993-84-6)
• EPA Substance Registry System: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylate(108993-84-6)

Safety Data

• Hazardous Substances Data: 108993-84-6(Hazardous Substances Data)

Upstream product

• 638-07-3 ethyl (2-chloroaceto)acetate 
• 504-02-9 1,3-cylohexanedione 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 

Downstream Products

• 132334-19-1 2-ethoxycarbonyl-3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran phenylhydrazone 
• 112579-43-8 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid 
• 132334-21-5 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran p-nitrophenylhydrazone 
• 3781-69-9 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester 
• 132334-20-4 2-ethoxycarbonyl-3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran p-nitrophenylhydrazone 

Relevant articles and documents

4-Hydroxy-3-methylbenzofuran-2-carbohydrazones as novel LSD1 inhibitors

Histone lysine specific demethylase 1 (LSD1 or KDM1A) is a potential therapeutic target in oncology due to its overexpression in various human tumors. We report herein a new class of benzofuran acylhydrazones as potent LSD1 inhibitors. Among the 31 compounds prepared, 14 compounds exhibited excellent LSD1 inhibitory activity with IC50 values ranging from 7.2 to 68.8 nM. In cellular assays, several compounds inhibited the proliferations of various cancer cell lines, including PC-3, MCG-803, U87 MG, PANC-1, HT-29 and MCF-7. This opens up the opportunity for further optimization and investigation of this class compounds for potential cancer treatment.

Diversity-Oriented Synthesis of Natural-Product-like Libraries Containing a 3-Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors

Natural products are a major source of biological molecules. The 3-methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host-plant resistance against insect pests. Herein, the diversity-oriented synthesis of a natural-product-like library is reported, in which the 3-methylfuran core is fused in an angular attachment to six common natural product scaffolds—coumarin, chalcone, flavone, flavonol, isoflavone and isoquinolinone. The structural diversity of this library is assessed computationally using cheminformatic analysis. Phenotypic high-throughput screening of β-glucuronidase activity uncovers several hits. Further in vivo screening confirms that these hits can induce resistance in rice to nymphs of the brown planthopper Nilaparvata lugens. This work validates the combination of diversity-oriented synthesis and high-throughput screening of β-glucuronidase activity as a strategy for discovering new chemical elicitors.

Understanding the Scope of Feist–Bénary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between α-Halo Ketones and β-Dicarbonyl Compounds

Feist–Bénary furan synthesis, the reaction between α-halocarbonyl and β-dicarbonyl compounds, has been known as an efficient method for generating many different types of furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal–Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from α-halo ketones and β-dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist–Bénary furan synthesis from α-halo ketones and β-dicarbonyl compounds without any base or solvent has also been developed.

Preparation and application of substituted benzofuran 2-formylhydrazone LSD1 inhibitor

The invention discloses a substituted benzofuran 2-formylhydrazone LSD1 inhibitor and a preparation method and an application thereof in tumor resistance. Specifically disclosed is a compound of formula (I) or a pharmaceutically acceptable salt thereof which has a good inhibitory effect on LSD1 enzyme. The invention further provides application of the compound shown in the formula (I) or the pharmaceutically acceptable salt thereof to treatment of diseases related to the expression quantity of the LSD1 enzyme, including but not limited to treatment of various cancers. The compound or the pharmaceutically acceptable salt thereof can be combined with other drugs (including but not limited to targeted drugs, various immunomodulators, anti-tumor antibodies and the like) to obtain a better cancer treatment effect.

Substituted benzofuran hydrazone derivative and preparation method thereof

The invention relates to the field of medical chemistry, and aims at providing a substituted benzofuran hydrazone derivative and a preparation method thereof. The product has a structure as shown in a formula (I), wherein B ring is selected from phenyl, furyl, thienyl and naphthyl; and R1, R2 and R3 are independently selected from hydrogen atoms, halogen, hydroxy, alkyl chain of C1-C7, alkoxy of C1-C7, nitryl or cyan. The benzofuran hydrazone derivative is a natural furan hydrazone derivative with a new frame, has potential medicinal activity; and the preparation of the compound can be used for supporting researches of benzofuran hydrazone medicinal activity. The preparation method is simple and easily available in steps, and has an important meaning for industrial production.

Furan flavone derivative and preparation method thereof

The invention relates to the field of medicine, and aims to provide a furan flavone derivative and a preparation method thereof. The furan flavonoid derivative is a furan flavone derivative having a furan ring substituted by methyl; the preparation method of the furan flavone derivative comprises the steps: uniformly dispersing two compounds defined in the specification and a weak base into a reaction solvent a, to obtain a raw material mixture; then carrying out a reaction of the raw material mixture at the temperature of 110 DEG C to 130 DEG C for 1 hour to 6 hours, and steaming to remove the reaction solvent, to obtain a crude product; and recrystallizing the crude product with ethanol, to obtain the furan flavone derivative. The furan flavone derivative is a natural furan flavone analogue having a novel skeleton, and has potential pharmaceutical activity; the preparation of the compound can provide a support for the pharmaceutical activity research on furan flavones, and the preparation method is simple in steps and low in loss rate, and has important significance for industrialized production.

Substituted furan isoflavone derivatives and its preparation method (by machine translation)

The present invention relates to the field of medicinal chemistry, and aims to provide a substituted furan isoflavone derivatives and its preparation method. The substituted furan isoflavone derivatives of formula (I) has the structure as illustrated, wherein R1 , R2 Each independently selected from hydrogen atom, methyl, methoxy or halogen. The product is a kind of has a new skeleton of natural furan isoflavone analogs, with potential pharmaceutical activity, the compounds of preparation can be furyl isoflavone pharmaceutical active research provide support; its preparation method step is simple, low loss rate. For the industrial production of important significance. (by machine translation)

Benzofuran fluoroflavanone derivative and preparation method thereof

The present invention relates to the field of pharmaceutical chemistry. A purpose of the present invention is to provide a benzofuran fluoroflavanone derivative and a preparation method thereof, wherein the product has a structure represented by a formula (I), the ring B is selected from phenyl or furyl, and R1, R2 and R3 are independently and respectively selected from hydrogen atom, halogen, cyano, nitro, a C1-C7 alkyl chain and C1-C7 alkoxy. According to the present invention, the benzofuran fluoroflavanone derivative is a class of the benzofuran flavone analogs having the new skeleton, and has potential pharmacological activity; the preparation of the compound can provide the support for the research of the pharmacological activity of the benzofuran flavone; and the preparation method has advantages of simple step and low loss rate, is the completely-new benzofuran flavone derivative synthesis route from the non-aromatic raw material, and provides important significance for the industrial production. The formula (I) is defined in the specification.

Substituted furan flavonol derivative and preparation method thereof

The invention relates to the field of medical chemistry, and aims at providing a substituted furan flavonol derivative and a preparation method thereof. The substituted furan flavonol derivative has a structure represented by formula (II) shown in the des

Alkali-free, solvent-free conditions through the Feist - Benary reaction process for preparing substituted furyl method (by machine translation)

The present invention provides a process for preparing multi-substituted furyl method, namely in alkali-free, under solvent-free conditions, α - halo with β - dicarbonyl compounds react multi-substituted furyl compound. The invention of the multi-substitu