873-95-0

Basic information

• Product Name: 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE
• Synonyms: 5,5-Dimethyl-3-aminocyclohex-2-enone;3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE;3-AMINO-5,5-DIMETHYLCYCLOHEX-2-EN-1-ONE;3-AMINO 5,5-DIMETHYL- CYCLOHEX-2-ENONE;3-Amino-5,5-dimethyl-2-cyclohexene-1-one;1-Amino-5,5-dimethylcyclohexene-3-one;3-azanyl-5,5-dimethyl-cyclohex-2-en-1-one
• CAS NO: 873-95-0
• Molecular Formula: C₈H₁₃NO
• Molecular Weight: 139.19
• Mol File: 873-95-0.mol
• Article Data: 32

Chemical Properties

• Melting Point: 165-167
• Boiling Point: 216.3 °C at 760 mmHg
• Flash Point: 84.6 °C
• Appearance: /
• Density: 0.992 g/cm³
• Vapor Pressure: 0.141mmHg at 25°C
• Refractive Index: 1.486
• PKA: 5.68±0.40(Predicted)
• CAS DataBase Reference: 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE(873-95-0)
• EPA Substance Registry System: 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE(873-95-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 873-95-0(Hazardous Substances Data)

Usage

General Description

3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE is a chemical compound with the molecular formula C9H15NO. It is a cyclic enamine, consisting of a cyclohexene ring with an amino group and two methyl groups attached at the 5 and 5 positions, and a ketone functional group at position 2. 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE is commonly used in organic synthesis and pharmaceutical research as a building block for various chemical reactions. It is also known to exhibit biological activity and is being studied for potential therapeutic applications.

InChI:InChI=1/C8H13NO/c1-8(2)4-6(9)3-7(10)5-8/h3H,4-5,9H2,1-2H3

Upstream product

• 126-81-8 dimedone 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 106-40-1 4-bromo-aniline 
• 106-47-8 4-chloro-aniline 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 62-53-3 aniline 
• 104-86-9 4-chlorobenzylamine 
• 2393-23-9 4-methoxy-benzylamine 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 104-94-9 4-methoxy-aniline 
• 3959-07-7 4-Bromobenzylamine 
• 100-46-9 benzylamine 
• 109-73-9 N-butylamine 
• 104-84-7 para-methylbenzylamine 

Downstream Products

• 23645-83-2 N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)acetamide 
• 23008-45-9 3-amino-5,5-dimethyl-cyclohex-2-enone-imine 
• 33365-81-0 2,2'-methylene-bis-(5,5-dimethyl-3-aminocyclohex-2-en-1-one) 
• 72431-36-8 3-Amino-5,5-dimethyl-2-(1-pyrrolidinylmethyl)-2-cyclohexen-1-on 
• 119022-19-4 4-hydroxy-7,7-dimethyl-3-phenyl-7,8-dihydrochinolin-2,5(1H,6H)-dion 
• 72431-33-5 3-Amino-5,5-dimethyl-2-piperidinomethyl-2-cyclohexen-1-on 
• 76159-33-6 3-Amino-2-hydroxymethyl-5,5-dimethyl-2-cyclohexen-1-on 
• 90043-96-2 3-crotonoylamino-5,5-dimethylcyclohex-2-enone 
• 90043-95-1 1,3-bis(5,5-dimethyl-3-oxocyclohex-1-enylamino)-3-methylpropan-1-one 
• 113859-91-9 5,5-Dimethyl-3-(1-methyl-2-oxo-2-phenyl-ethylamino)-cyclohex-2-enone 
• 96797-03-4 5,6,7,8-tetrafluoro-2,2-dimethylbenzo<2,1-b>quinoline-4-one 
• 96797-04-5 3-Amino-2-(hydroxy-pentafluorophenyl-methyl)-5,5-dimethyl-cyclohex-2-enone 
• 113859-94-2 3,6,6-Trimethyl-2-phenyl-1,5,6,7-tetrahydro-indol-4-one 
• 113859-88-4 5,5-Dimethyl-3-(2-oxo-1-phenyl-propylamino)-cyclohex-2-enone 

Relevant articles and documents

Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.

SHP2 INHIBITORS, COMPOSITIONS AND USES THEREOF

Provided are compounds of Formula (I), methods of using the compounds as SHP2 inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating SHP2-mediated diseases.

Cu catalyzed cross-dehydrogenative coupling reaction for the synthesis of 3-hydroxy-2-pyrrolidinones

A new convenient strategy for the synthesis of 3-hydroxy-2-pyrrolidinone derivatives featuring regioselective C–C coupling has been developed. This is a Cu (II) catalyzed cross dehydrogenative coupling (CDC) involving enamino-ketones of benzyl amines and di-alkyl acetylenedicarboxylate, followed by cyclization by primary amines. TBHP (tert-butyl hydroperoxide) has been used as the oxidant to promote the coupling protocol. This synthetic route principally demonstrates the scope of CDC reaction and also applicable to gram-scale synthesis.