3864-08-2

Basic information

• Product Name: 5H-dibenzo[c,e]azepine-5,7(6H)-dione
• CAS NO: 3864-08-2
• Molecular Formula: C₁₄H₉NO₂
• Molecular Weight: 223.2268
• Mol File: 3864-08-2.mol

Chemical Properties

• Boiling Point: 460.8°C at 760 mmHg
• Flash Point: 201.7°C
• Density: 1.291g/cm³
• Vapor Pressure: 1.13E-08mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: 5H-dibenzo[c,e]azepine-5,7(6H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-dibenzo[c,e]azepine-5,7(6H)-dione(3864-08-2)
• EPA Substance Registry System: 5H-dibenzo[c,e]azepine-5,7(6H)-dione(3864-08-2)

Safety Data

• Hazardous Substances Data: 3864-08-2(Hazardous Substances Data)

Upstream product

• 6050-13-1 biphenyl-2,2'-dicarboxylic acid anhydride 
• 17356-08-0 thiourea 
• 57-13-6 urea 
• 39950-05-5 [1,1'-biphenyl]-2,2'-dicarboxamide 
• 6747-35-9 2-carboxy-2'-(aminocarboxyl)-1,1'-biphenyl 
• 14140-04-6 phenanthrene-9,10-dione oxime 
• 854645-29-7 diphenic acid bis-thio ureide 
• 84-11-7 9,10-phenanthrenequinone 
• 863305-32-2 diphenic acid 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 
• 94194-32-8 N-(2-phenylallyl)biphenyl-2,2'-dicarboximide 
• 7719-09-7 thionyl chloride 
• 55-21-0 benzamide 

Downstream Products

• 6672-69-1 6,7-dihydro-5H-dibenzo[c,e]azepine 
• 6223-83-2 9-oxo-9H-fluorene-4-carboxylic acid 
• 42135-38-6 9-fluorenone-4-carbonyl amide 
• 100891-98-3 N-benzyldiphenimide 
• 125030-72-0 6-{3-[4-(2-Chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-dibenzo[c,e]azepine-5,7-dione 
• 94230-27-0 6-Ethyl-5H-dibenzazepine-5,5,7-d3 
• 94230-26-9 6-Ethyl-5H-dibenzazepine-5,5,7-d3 

Relevant articles and documents

Hypolipidemic activity of phthalimide derivatives V: Reduced and hydrolytic products of simple cyclic imides

A series of cyclic imides and related compounds have previously been shown to possess hypolipidemic activity at the low dose level of 20 mg/kg/d. Hydrolytic and reduced products of the cyclic imides were synthesized and examined to discern if possible metabolic products were the active chemical species of these hypolipidemic agents. Phthalimide proved to be the most active cyclic imide tested. Unfortunately, the new products did not, in general, improve hypolipidemic activity in rodents. The exceptions were piperidine which demonstrated improved hypotriglyceridemic activity, and 3,4,5,6-dibenzohomopiperidin-2-one, which demonstrated improved hypocholesterolemic activity compared to phthalimide.

Synthesis of 5H-Dibenzo[c,e]azepine-5,7(6H)-diones from Benzamides via Palladium-Catalyzed Double C-H Bond Activation

A convenient and efficient method for the synthesis of 5H-dibenzo[c,e]azepine-5,7(6H)-diones from simple and readily available benzamides is described in this work. The palladium-catalyzed homocoupling of benzamides occurred via ortho-selective double C-H bond activation using the simplest amide CONH2 as a directing group. The subsequent intramolecular condensation reaction proceeded smoothly to produce 5H-dibenzo[c,e]azepine-5,7(6H)-diones in satisfactory to excellent yields in one pot.

Preparation method of dibenzo [c, e] aza-5, 7 (6H)-dione compound

The invention belongs to the field of medical and chemical intermediates and related chemical technology, and relates to a preparation method of a dibenzo [c, e] aza-5, 7 (6H)-dione compound. The dibenzo [c, e] aza-5, 7 (6H)-dioneis an important bioactive molecule, has a skeleton structure frequently appearing in a pharmaceutical molecule, has better effects on reducing blood fat, treating obesity, resisting epinephrine and the like, can be significantly applied in the fields such as organic synthesis and pharmaceutical chemistry, and has a wide market prospect. According to the preparation method of the dibenzo [c, e] aza-5, 7 (6H)-dione compound provided by the invention, benzamide is adopted as a raw material, and a series of dibenzo [c, e] aza-5, 7 (6H)-dikone and a derivative thereof are synthesized under the action of a palladium catalyst. The method has the advantages of short synthetic route, simplicity in operation, higher yield and the like. The preparation method of the dibenzo [c, e] aza-5, 7 (6H)-dione compound provided by the invention has a larger use value and social and economic benefits.

A facile synthesis of 6-alkyl-6,7-dihydro-5H-dibenz[c,e]azepines: Potent hypolipidemics

6-Alkyl-6,7-dihydro-5H-dibenz[c,e]azepines were synthesized in two steps in 63-88% overall yield by utilizing an efficient borane-tetrahydrofuran reduction of imides.

Photochemical Electron-transfer Reactions of Biphenyl-2,2'-dicarboximide and Naphthalene-1,8-dicarboximide with Olefin. Dependence of the Reaction Course on the Structure of the Aromatic Imide

Photoreactions of N-methylbiphenyl-2,2'-dicarboximide and N-ethylnaphthalene-1,8-dicarboximide (2) with 1,1-diphenylethylene (3) in methanol gave methanol-incorporated 1:1:1-adduct (7) and 2,2-diphenylethyl methyl ether (6), an anti-Markovnikov adduct of methanol to 3.The ratio of the two types of products largely depends on the structure of the aromatic imides.Probably the spin densities of the radical anions of the aromatic imides seem to play an important role to determine the reaction courses after the photochemical electron-transfer process.Similar results were obtained in the photoreaction of N-(2-phenylallyl)aromatic imides; elimination induced by methanol-incorporation vs. anti-Markovnikov addition of methanol. Photoreactions of N-(trans-3-phenylallyl) aromatic imides in methanol gave methanol-incorporated O-cyclized products (20 and 27) and C-cyclized products (21 and 28).A tentative mechanism for the O-cyclization is proposed; i.e., intramolecular electron transfer followed by anti-Markovnikov addition of methanol to the radical cation of the double bond moiety, nucleophilic attack of the aromatic imide radical anion moiety, secondary electron-transfer, and then polar addition of methanol.

Comparison of the hypolipidemic activity of cyclic vs. acyclic imides

Two series of nitrogen-substituted cyclic and acyclic imides were examined for hypolipidemic activity in mice after dosing for 16 days at a dose of 20 mg/kg per day. The hypolipidemic activity of the unsubstituted, N-butyl, N-3-oxobutyl, and N-2-carboxyethyl derivatives of diacetimide and succinimide were compared as well as the unsubstituted and N-substituted dibenzimide and diphenimide. It was shown that an imide functionally incorporated into a ring was not necessary for hypocholesterolemic activity. Good hypocholesterolemic activity was observed in both series of acyclic and cyclic imides. However, a cyclic imido structure was a necessary requirement for good hypotriglyceridemic activity. A decrease in hypotriglyceridemic activity was noted when comparing the cyclic imides to their respective acyclic congeners.

Hypolipidemic activity of N-substituted diphenimides in rodents

A number of N-substituted diphenimide derivatives were investigated for hypolipidemic activity in mice at 20 mg/kg/day I.P. A number of the compounds were found to be more active than clofibrate and equally as active as other cyclic imides reported previously in the literature. N-(4-Methylphenyl)-diphenimide demonstrated the most potent acitivity lowering serum cholesterol levels by 48% and serum triglyceride levels by 40% after 16 days administration of drug.