112677-05-1

Basic information

• Product Name: 3-DIMETHYLAMINO-1-(5-METHYL-FURAN-2-YL)-PROPENONE
• Synonyms: 3-(DIMETHYLAMINO)-1-(5-METHYL-2-FURYL)-2-PROPEN-1-ONE;3-DIMETHYLAMINO-1-(5-METHYL-FURAN-2-YL)-PROPENONE;3-(DIMETHYLAMINO)-1-(5-METHYLFURAN-2-YL)PROP-2-EN-1-ONE
• CAS NO: 112677-05-1
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.22
• Mol File: 112677-05-1.mol

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 261.8±40.0 °C(Predicted)
• Appearance: /
• Density: 1.051±0.06 g/cm3(Predicted)
• PKA: 6.42±0.70(Predicted)
• CAS DataBase Reference: 3-DIMETHYLAMINO-1-(5-METHYL-FURAN-2-YL)-PROPENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DIMETHYLAMINO-1-(5-METHYL-FURAN-2-YL)-PROPENONE(112677-05-1)
• EPA Substance Registry System: 3-DIMETHYLAMINO-1-(5-METHYL-FURAN-2-YL)-PROPENONE(112677-05-1)

Safety Data

• Hazardous Substances Data: 112677-05-1(Hazardous Substances Data)

Upstream product

• 1193-79-9 2-acetyl-5-methylfuran 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Relevant articles and documents

[2+2] Cycloaddition of electron-poor acetylenes to (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones: synthesis of highly functionalized 1-heteroaroyl-1,3-butadienes

Microwave-assisted [2+2] cycloaddition of (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones to dimethyl acetylenedicarboxylates gives (2E,3E)-dimethyl-2-[(dimethylamino)methylene]-3-(substituted)succinates in 8-91% yield. In the case of a 4,5-dihydrothiazoline derivative, cycloaddition also took place at the endocyclic C{double bond, long}N double bond.

Experimental and theoretical investigation of new furan and thiophene derivatives containing oxazole, isoxazole, or isothiazole subunits

Herein, we present joint experimental and theoretical studies on newly designed thiophene- or furan-based oxazole, isoxazole, and isothiazole derivatives. Our synthetic approach towards the preparation of target compounds is based on Van Leusen reaction. By following this reaction, oxazoles (1 and 2) containing the pertinent heterocyclic systems were obtained from the reaction of suitable furan or thiophene derivatives with tosylmethyl isocyanide (TOSMIC). Hereby, three ring systems of furan or thiophene, linked to the oxazole rings at their 2- and 5-positions (3 and 4), were also successfully synthesized for the first time. Reaction of the starting materials containing acetyl groups in their 2-position with dimethyl acetal and following the treatment by hydroxylamine hydrochloride, desired isoxazole derivatives (5 and 6), were obtained. Additionally, isothiazole derivatives (7 and 8) were prepared by following the similar approach to the isoxazole synthesis. Whole of these cyclization reactions occurred with good to excellent yields. Structural analyses of the synthesized compounds were performed by appropriate spectroscopic methods (UV-vis, FT-IR, LC-MS, 1H-NMR, 13C-NMR, and elemental analysis). We also carried out theoretical studies for identifying the structure-activity relationship and determining chemical properties of the studied molecules. For this purpose, we obtained information about structural properties (bond lengths, bond angles, dihedral angles, and dipole moments), band gap energies, and spectroscopic characteristics (UV-vis, FT-IR, 1H-NMR, and 13C-NMR) of the target compounds. [Figure not available: see fulltext.].

Design, synthesis, and preliminary bioactivity evaluation of N-benzylpyrimidin-2-amine derivatives as novel histone deacetylase inhibitor

Histone deacetylase (HDAC) inhibitors have been identified for the treatment of cancer. Lately, we designed and synthesized a series of substituted N-benzylpyrimidin-2-amine derivatives as potent HDAC inhibitors. In vitro HDAC inhibitory activities and an

Pyrimidine phenmethyl different hydroxy wo acid histone deacetylase inhibitors and preparation method and application

The invention discloses a pyrimidine benzyl hydroxamic acid histone deacetylase inhibitor, and a preparation method and application thereof. The compound has the structure shown as general formula I. The compound provided by the invention has relatively high inhibiting activity on histone deacetylases, and can be used for preparing medicaments for preventing or treating related mammalian diseases caused by abnormal expression of the histone deacetylases. The invention further relates to the pharmaceutical application of the compound with the structure shown as the general formula I.

First examples of 2,6-diarylnicotinaldehydes prepared under conventional and microwave conditions

Enaminoketones undergo unexpected self condensation in acetic acid to produce a wide range of 2,3,6-trisubstituted pyridine derivatives in excellent yields in the presence of NH4OAc. This is the first Letter on the synthesis of 2,6-diarylnicoti

Efficient organocatalytic dual activation strategy for preparing the versatile synthons (2 E)-1-(Het)aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene]cycloalkanones

A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3- (dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene] cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an -methylene moiety with N,N-dimethylformamide dimethyl acetal at 100 C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields. Georg Thieme Verlag Stuttgart - New York.

Biological evaluation of isoegomaketone isolated from perilla frutescens and its synthetic derivatives as anti-inflammatory agents

The anti-inflammatory activities of a prepared isoegomaketone 3a and its derivatives 3b-3f were evaluated in RAW 264.7 cells. Among these, the compound 3d was displayed the most potent inhibitory activities against production of nitric oxide, monocyte chemoattractant protein- 1 and interleukin-6. Based on these results, the abilities of compounds 3a-3f to modulate NF-κB and AP-1-mediated gene transcription using a luciferase reporter assay were investigated. The transcriptional activities of NF-κB and AP-1 decreased when pretreated with 3a- 3f. Interestingly, at 10 μM, compound 3d markedly suppressed the lipopolysaccharide-induced NF-κB and activator protein-1 DNA binding activities. Some preliminary structure-activity relationships were proposed that may provide a direction for further study.

Preparation of Substituted N-Phenyl-4-aryl-2-pyrimidinamines as Mediator Release Inhibitors

The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders.Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy.Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release.These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines.After examining a large number of analogs, N--4-(2-pyridinyl)-2-pyrimidinamine (1-27) was chosen for toxicological evaluation.

4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines

This disclosure describes novel 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines having anti-asthmatic activity.