6333-22-8

Usage

Type of compound

Cyclic ketone

Structural features

+ Contains two dimethylamino groups
+ Attached to a cyclopentanone ring

Uses

+ Reagent in organic synthesis
+ Building block for pharmaceuticals and agrochemicals
+ Chiral auxiliary in asymmetric synthesis
+ Precursor for synthesis of heterocyclic compounds
+ Potential use in new material development and medicinal chemistry

Upstream product

• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 120-92-3 cyclopentanone 
• 124-40-3 dimethyl amine 

Relevant academic research and scientific papers

METHOD FOR PRODUCING 5-NORBORNENE-2-SPIRO-ALPHA-CYCLOALKANONE- ALPHA'-SPIRO-2''-5''-NORBORNENE

A method for producing a 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene, comprising: a first step of forming a specific Mannich base by reacting a specific carbonyl compound and a specific amine compound with each other in an acidic solvent comprising a formaldehyde derivative and an acid represented by a formula: HX (in the formula, X represents F or the like), to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent; and a second step of reacting the Mannich base and a specific diene compound with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 mole equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form a specific 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene, wherein a content of the acid in the acidic solvent used in the first step is 0.01 to 0.075 mole equivalents to the ketone group of the carbonyl compound.

Evaluation of net antioxidant activity of mono- and bis-Mannich base hydrochlorides and 3-keto-1,5-bisphosphonates from their ProAntidex parameter

Abstract A series of mono- and bis-Mannich base hydrochlorides and of 3-keto-1,5-bisphosphonates were prepared and characterized on the basis of their infrared (IR), 1H, 13C and 31P NMR spectral data. All the title compounds were tested for their in vitro antioxidant activities by 1,1-diphenyl-2-picrylhydrazyl (DPPH), H2O2, hydroxyl radical and Ferric Reducing Power (FRP) methods. The antioxidant activity of these compounds was analyzed simultaneously with their pro-oxidant capacity. The ratio of pro-oxidant to the antioxidant activity (ProAntidex) represents a useful index of the net free radical scavenging potential of the synthesized compounds. Ferrous, calcium and magnesium ion chelating abilities were also evaluated. All the tested compounds showed significant antioxidant activity and high ProAntidex.

ALICYCLIC MONOEPOXY-MONOOL COMPOUND HAVING BIS-SPIRONORBORNANE STRUCTURE, AND METHOD FOR PRODUCING THE SAME

PROBLEM TO BE SOLVED: To provide a novel alicyclic monoepoxy-monool compound useful as an intermediate of medicine, an intermediate material for industrial products, and an additive; and to provide a method for producing the same. SOLUTION: Problems are solved through: the synthesis and identification of an alicyclic monoepoxy-monool compound having a cycloalkanone bis-spironorbornane structure represented by the following general formula (1); the review of a production method; and the analysis of a reaction intermediate. In the formula, one of R1 and R2 is -OH and the other thereof is -H; R3 and R4 are each independently the one selected from the group consisting of a hydrogen atom, 1-10C alkyl group, and a fluorine atom; and n is an integer of 2 to 5. COPYRIGHT: (C)2016,JPOandINPIT

ALICYCLIC AMINE COMPOUND OBTAINED BY DIMERIZATION AND TRIMERIZATION OF ALICYCLIC DIOL HAVING BIS-SPIRONORBORNANE STRUCTURE, AND METHOD FOR PRODUCING THE SAME

PROBLEM TO BE SOLVED: To provide an alicyclic amine compound capable of being used as an intermediate of medicine, an intermediate material for industrial products, and an additive; and to provide a method for producing the same. SOLUTION: This invention relates to: an alicyclic secondary amine compound having a bis-spironorbornane structure represented by the chemical formula (1); and further a tertiary amine compound having another bis-spironorbornane structure. These are produced through reaction of bis-spironorbornyl ketone having hydroxyl with ammonia. In the formula, one of R1, R2, R3, and R4 is the one selected from a hydroxyl, keto, imino, and amino group, and others thereof are hydrogen; and n is an integer of 2 to 5. COPYRIGHT: (C)2016,JPOandINPIT

METHOD FOR MANUFACTURING 5-NORBORNENE-2-SPIRO-α-CYCLOALKANONE-α'-SPIRO-2''-5''-NORBONENES AND METHOD FOR MANUFACTURING MANNICH BASE

PROBLEM TO BE SOLVED: To provide a method for manufacturing 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2''-5''-norbonenes capable of manufacturing 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2''-5''-norbonenes at high level yield and efficiency. SOLUTION: There is provided a method for manufacturing 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2''-5''-norbonenes including a first process of reacting a specific carbonyl compound with a specific amine compound in an acidic solvent containing a first organic solvent which has the boiling point of 85 to 110°C and Mannich base does not solve, a formaldehyde derivative and an acid represented by the formula:HX, where X represents one kind selected from a group consisting of F, Cl, Br, I, CH3COO, CF3COO, CH3SO3, CF3SO3, C6H5SO3, CH3C6H4SO3, HOSO3 and H2 PO4 with the concentration of the acid of 0.01 mol/L or more and forming a specific Mannich base to obtain a reaction solution containing the Mannich base in the acidic solvent and a second process of adding a second organic solvent, a base of 1.0 to 20.0 times to the acid and a specific diene compound to the acid, heating and reacting the Mannich base and the diene compound to obtain specific 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2''-5''-norbonenes. COPYRIGHT: (C)2015,JPO&INPIT

ALICYCLIC DIAMINE COMPOUND HAVING BIS-SPIRONORBORNANE STRUCTURE, METHOD FOR PRODUCING THE SAME, AND USE THEREOF

PROBLEM TO BE SOLVED: To provide: an alicyclic diamine compound that is a multifunctional compound capable of being used for a polymer material formed through condensation reaction or curing reaction and that provides a polymer material excellent in transparency and thermal resistance; a method for producing the same; and a production intermediate. SOLUTION: Problems are solved through: the synthesis and identification of an alicyclic diamine compound having a bis-spironorbornane structure represented by the following general formula (1); and the review of a production method and use thereof as a reaction intermediate. In the formula, one of R1 and R2 is -NH2 and the other thereof is -H; one of R3 and R4 is -NH2 and the other thereof is -H; R5 and R6 are each independently the one selected from the group consisting of a hydrogen atom, 1-10C alkyl group, and a fluorine atom; and n is an integer of 2 to 5. COPYRIGHT: (C)2016,JPO&INPIT

5-NORBORNENE-2-SPIRO-a-CYCLOALKANONE-a'-SPIRO-2''-5''-NORBORNENE AND METHOD FOR PRODUCING THE SAME

A 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene represented by the following general formula (1): [in the formula (1), R1s, R2, and R3 each independently represent a hydrogen atom or the like, and n represents an integer of 0 to 12].

NORBORNANE-2-SPIRO- A-CYCLOALKANONE-A '-SPIRO-2''-NORBORNANE-5,5'',6,6''-TETRACARBOXYLIC DIANHYDRIDE, NORBORNANE-2-SPIRO- A-CYCLOALKANONE-A '-SPIRO-2''-NORBORNANE-5,5'',6,6''-TETRACARBOXYLIC ACID AND ESTER THEREOF, METHOD FOR PRODUCING NORBORNANE-2-SPIRO-

A norbornane-2-spiro-α-cycloalkanone-α'-spiro-2"-norbor nane-5,5",6,6"-tetracarboxylic dianhydride represented by the following general formula (1): [in the formula (1), n represents an integer of 0 to 12, and R1s, R2, R3

Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity

A number of Mannich bases of cycloalkanones and related quaternary ammonium compounds were prepared for cytotoxic evaluation in order to examine the theory that sequential release of alkylating agents produces increased bioactivity compared to related compounds containing only 1 potential alkylating site.Many of the compounds had significant activity against murine L1210 cells and various human tumours.Some correlations between structure and activity were noted but the biological data did not support the view that potential sequential liberation of cytotoxic species produced compounds with increased potency.The formation of various oximes and oxime benzoates as candidate prodrugs was achieved but in general these compounds were not cytotoxic at the concentrations utilized.This observation may be due to the fact that the oximes were much more stable in deuterated phosphate buffered saline over a period of 48 h at 37 deg than the Mannich bases, as revealed by 1H-NMR spectroscopy. Mannich bases / cytotoxic evaluations / prodrugs / 1H-NMR spectroscopy / structure-activity relationships