29974-49-0

Basic information

• Product Name: 5,5-dimethyl-2-[(phenylamino)methylidene]cyclohexane-1,3-dione
• Synonyms: 1,3-Cyclohexanedione, 5,5-dimethyl-2-[(phenylamino)methylene]-; 2-(Anilinomethylene)-5,5-dimethylcyclohexane-1,3-dione
• CAS NO: 29974-49-0
• Molecular Formula: C₁₅H₁₇NO₂
• Molecular Weight: 243.301
• Mol File: 29974-49-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 378.9°C at 760 mmHg
• Flash Point: 141.1°C
• Density: 1.201g/cm³
• Vapor Pressure: 6.09E-06mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 5,5-dimethyl-2-[(phenylamino)methylidene]cyclohexane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-2-[(phenylamino)methylidene]cyclohexane-1,3-dione(29974-49-0)
• EPA Substance Registry System: 5,5-dimethyl-2-[(phenylamino)methylidene]cyclohexane-1,3-dione(29974-49-0)

Safety Data

• Hazardous Substances Data: 29974-49-0(Hazardous Substances Data)

Upstream product

• 126-81-8 dimedone 
• 864131-95-3 N,N'-diphenylformamidine 
• 122-51-0 orthoformic acid triethyl ester 
• 62-53-3 aniline 
• 6780-49-0 ethyl N-phenylformimidate 
• 75039-59-7 2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 

Downstream Products

• 100185-94-2 N,N'-Bis-<(4,4-dimethyl-2,6-dioxocyclohexyliden)-methylen>-1,7-diamino-4-aza-heptan 
• 112146-77-7 methyl 2-deoxy-2-<(4,4-dimethyl.2,6-dioxocyclohexylidenemethyl)amino>-β-D-glucopyranoside 
• 112146-75-5 methyl 2-deoxy-2-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α-D-glucopyranoside 
• 32583-56-5 2-(aminomethylene)-5,5-dimethylcyclohexane-1,3-dione 
• 40756-30-7 3-hydroxy-2,5,5-trimethylcyclohex-2-en-1-one 
• 105244-30-2 2-(3,3-Bis-dimethylamino-allylidene)-5,5-dimethyl-cyclohexane-1,3-dione 
• 303013-99-2 7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 111286-56-7 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-[(4,4-dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-tetrahydro-pyran-4-yl ester 
• 112146-76-6 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[(4,4-dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-6-methoxy-tetrahydro-pyran-4-yl ester 
• 112146-86-8 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-benzyloxy-5-[(4,4-dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-tetrahydro-pyran-4-yl ester 
• 112146-82-4 Acetic acid (2R,3R,4R,5S)-5-allyloxy-2-((S)-1,2-diacetoxy-ethyl)-4-[(4,4-dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-tetrahydro-furan-3-yl ester 
• 112146-84-6 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-allyloxy-5-[(4,4-dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-tetrahydro-pyran-4-yl ester 
• 112146-85-7 benzyl 2-deoxy-2-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α-D-glucopyranoside 
• 112146-81-3 allyl 2-deoxy-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α-D-glucofuranoside 

Relevant articles and documents

Synthesis, crystal structures, spectroscopic, and cytotoxicity study of Cu(II), Co(II), Ni(II) and Pd(II) complexes with 2-anilinomethylidene-5,5-dimethylcyclohexane-1,3-dione

The coordination compounds of Cu(II), Co(II), Ni(II) and Pd(II) with 2-anilinomethylidene-5,5-dimethylcyclohexane-1,3-dione (HL) of the composition [ML2(C2H5OH)2]·nH2O (M = Co (n = 1), Ni (n = 0)) and

Uses of dimedone to synthesis pyrazole, isoxazole and thiophene derivatives with antiproliferative, tyrosine kinase and Pim-1 kinase inhibitions

We are aiming in this work to synthesize target molecules not only possess antitumor activities but also kinase inhibitors. The target molecules were obtained from dimedone, which reacted with triethoxymethane to produce a product that is capable for many heterocyclization reactions to give fused pyrazole, thiophene and isoxazole derivatives. Compounds 7b, 7c, 7d, 9b, 11, 12c, 12d, 14b, 16b, 17c, 17d, 18c, 18d, and 18e were the most cytotoxic compounds, their further tests toward the five tyrosine kinases c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR and Pim-1 kinase showed that compounds 7b, 7d, 11, 12c, 14b, 16b, 17d, 18d, and 18e were the most potent of the tested compounds toward the five tyrosine kinases and compounds 7b, 7d, 14b, 16b, and 18e were of the highest inhibitions toward Pim-1 kinase. PAINS the most cytotoxic compounds showed zero PAINS alert, therefore, these compounds can be used as useful drugs in the future.

Development of Inhibitors of Salicylic Acid Signaling

Salicylic acid (SA) plays important roles in the induction of systemic acquired resistance (SAR) in plants. Determining the mechanism of SAR will extend our understanding of plant defenses against pathogens. We recently reported that PAMD is an inhibitor of SA signaling, which suppresses the expression of the pathogenesis-related PR genes and is expected to facilitate the understanding of SA signaling. However, PAMD strongly inhibits plant growth. To minimize the side effects of PAMD, we synthesized a number of PAMD derivatives, and identified compound 4 that strongly suppresses the expression of the PR genes with fewer adverse effects on plant growth than PAMD. We further showed that the adverse effects on plant growth were partially caused the stabilization of DELLA, which is also related to the pathogen responses. These results indicate that compound 4 would facilitate our understanding of SA signaling and its cross talk with other plant hormones.