1107608-80-9

Basic information

• Product Name: (S) QuinoxP(R)
• Synonyms: (S) QuinoxP;QuinoxP;(S,S)-QuinoxP*;2,3-Bis[(S)-(1,1-dimethylethyl)methylphosphino]quinoxaline;(S,S)-(+)-2,3-Bis(t-butylmethylphosphino)quinoxaline;(S) QuinoxP(R);(S,S)-2,3-Bis(tert-butylmethylphosphino)quinoxaline;3-bis((S)-tert-butyl(methyl)phosphino)quinoxaline
• CAS NO: 1107608-80-9
• Molecular Formula: C₁₈H₂₈N₂P₂
• Molecular Weight: 334.375842
• Product Categories: Chiral Phosphine
• Mol File: 1107608-80-9.mol

Chemical Properties

• Melting Point: 100-105 °C
• Boiling Point: 447.6±45.0 °C(Predicted)
• Appearance: orange/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.54±0.59(Predicted)
• CAS DataBase Reference: (S) QuinoxP(R)(CAS DataBase Reference)
• NIST Chemistry Reference: (S) QuinoxP(R)(1107608-80-9)
• EPA Substance Registry System: (S) QuinoxP(R)(1107608-80-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 1107608-80-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S) QuinoxP(R) is used as a key reagent for the synthesis of chiral tetraphenylenes, which are important building blocks in the development of pharmaceuticals with specific biological activities. The chiral nature of these compounds allows for the creation of enantiomerically pure drugs, which can have different therapeutic effects and reduce potential side effects.
Used in Chemical Industry:
(S) QuinoxP(R) is used as a versatile reagent for the synthesis of fused lactones and other useful intermediates in the chemical industry. These intermediates can be further processed or modified to produce a wide range of chemical products, including specialty chemicals, agrochemicals, and materials for various applications.
Used in Organic Synthesis Research:
(S) QuinoxP(R) is used as a research tool in organic synthesis to explore new reaction pathways, develop innovative synthetic methods, and discover novel compounds with potential applications in various fields. Its unique properties and reactivity make it an attractive candidate for studying new chemical transformations and understanding the underlying mechanisms.

Reaction

Ligand for the rhodium-catalyzed, asymmetric hydrogenation of dehydroamino acid esters and α-enamides. Ligand for the rhodium-catalyzed, asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds. Ligand for the rhodium-catalyzed, asymmetric alkylative ring opening reaction Ligand for the palladium-catalyzed asymmetric allylic alkylation and amination of racemic substrates. Ligand for the ruthenium-catalyzed asymmetric hydrogenation of ketones. Ligand for the rhodium-catalyzed, asymmetric hydroacylation of 1,1-disubstituted alkenes with aldehydes. Ligand for the silver-catalyzed asymmetric nitroso aldol reaction.

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 281667-49-0 (R)-tert-butyl(hydroxymethyl)methylphosphine borane 
• 920505-31-3 C₁₈H₃₄B₂N₂P₂ 
• 263768-77-0 (±)-tert-butylmethylphosphine borane 
• 263563-97-9 (-)-(R)-tert-butylmethylphosphine-borane 
• 281667-49-0 (rac)-tert-butyl(hydroxymethyl)methylphosphine borane 
• 263563-97-9 (S)-(tert-butyl)(methyl)phosphine-borane 
• 1338825-24-3 C₁₈H₃₄B₂N₂P₂ 

Downstream Products

• 1313600-56-4 bis-[2,3-bis(tert-butylmethylphosphino)quinoxaline]gold(I) chloride 
• 959705-17-0 bis(2,3-bis(tert-butylmethylphosphino)quinoxaline)aurate(I) chloride 
• 1355199-46-0 [Rh((R,R)-QuinoxP*)(cod)]SbF₆ 
• 952023-91-5 [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride 
• 1355199-46-0 [Rh((S,S)-QuinoxP*)(cod)]SbF₆ 
• 1228170-55-5 (p-fluorophenyl)(pentafluorophenyl)((R,R)-(-)-2,3-bis(tert-butylmethylphosphino)qinoxaline)platinum(II) 
• 952023-91-5 ((R,R)-(-)-2,3-bis(tert-butylmethylphosphino)quinoxaline)dichloropalladium(II) 
• 1007582-83-3 ((R,R)-(-)-2,3-bis(tert-butylmethylphosphino)quinoxaline)dichloroplatinum(II) 
• 1007582-87-7 ((R,R)-(-)-2,3-bis(tert-butylmethylphosphino)quinoxaline)tricarbonylchlororhenium 
• 1313600-56-4 bis(2,3-bis(tert-butylmethylphosphino)quinoxaline) gold (I) chloride 

Relevant articles and documents

An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions

A new P-chiral phosphine ligand, (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline, has been prepared by the reaction of enantiomerically pure tert-butylmethylphosphine-borane with 2,3-dichloroquinoxaline. This ligand, in contrast to most of the previously reported P-chiral ligands, is an air-stable solid and exhibits excellent enantioselectivities in both Rh-catalyzed asymmetric hydrogenations and Rh- or Pd-catalyzed carbon-carbon bond-forming reactions. Copyright

Efficient Preparation of (S)- and (R)- tert -Butylmethylphosphine-Borane: A Novel Entry to Important P-Stereogenic Ligands

A novel one-pot reductive methodology for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The preparation uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the reduction of a mixed anhydride, the configurational stability of which has been studied in several solvents and temperatures. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodology, the product obtained in this manner was used in the preparation of Quinox-P?.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2, 3-BISPHOSPHINOPYRAZINE DERIVATIVE AND METHOD FOR PRODUCING OPTICALLY ACTIVE PHOSPHINE TRANSITION METAL COMPLEX

In the method for producing an optically active 2,3-bisphosphinopyrazine derivative of the present invention, an optically active 2,3-bisphosphinopyrazine derivative represented by the following formula (3) is produced by the step of: preparing solution A containing 2,3-dihalogenopyrazine represented by the following formula (1) and a carboxylic acid amide coordinating solvent, lithiating an optically active R- or S-isomer of a hydrogen-phosphine borane compound represented by the following formula (2) to give a lithiated phosphine borane compound; adding solution B containing the lithiated phosphine borane compound to the solution A to perform an aromatic nucleophilic substitution reaction; and then performing a deboranation reaction. (For symbols in the formulas, see the description.)

METHOD FOR PRODUCING 2,3-BISPHOSPHINOPYRAZINE DERIVATIVE, AND METHOD FOR PRODUCING PHOSPHINE TRANSITION METAL COMPLEX

There is provided a method for producing a 2,3-bisphosphinopyrazine derivative, the method comprising a first step of adding a base to a liquid comprising: 2,3-dihalogenopyrazine represented by the following general formula (1); a hydrogen-phosphine borane compound represented by the following general formula (2); and a deboranating agent, and allowing the resultant to react to thereby obtain the 2,3-bisphosphinopyrazine derivative represented by the following general formula (3). According to the present invention, a method for producing the industrially advantageous 2,3-bisphosphinopyrazine derivative can be provided.

Anticancer agent composition

Provided is an anti-cancer agent composition exhibiting excellent solubility and exerting high anti-cancer activity while exhibiting low toxicity. An anti-cancer composition characterized by containing a cyclodextrin compound and a phosphine transition metal complex represented by general formula (1). (In the formula, R1 and R2 represent a linear or branched alkyl group, a cycloalkyl group, a cycloalkyl group having a substituent, an adamantyl group, a phenyl group, or a phenyl group having a substituent, have a carbon number between 1 and 10, and may represent the same group or different groups. R3 and R4 represent a hydrogen atom or a linear or branched alkyl group, have a carbon number between 1 and 6, and may represent the same group or different groups. R3 and R4 may form a saturated or unsaturated ring by bonding to one another and said saturated or unsaturated ring may have a substituent. M represents a transition metal atom selected from among gold, copper, and silver. X- represents an anion.)

ANTI-CANCER AGENT

The anti-cancer agent of the present invention contains at least one kind of phosphine transition metal complex selected from a group of compounds represented by the following Formulae (1a) to (1d). According to this anti-cancer agent, an anti-cancer agent is provided which has a higher anti-cancer activity and lower toxicity compared to anti-cancer agents in the related art. In Formulae (1a), (1b), (1c), and (1d), R1 and R2 represent a linear or branched alkyl group, and R4 has a higher priority than R2 as ranked according to RS notation. R3 and R4 represent a hydrogen atom or a linear or branched alkyl group. M represents an atom of a transition metal selected from a group consisting of gold, copper, and silver. X? represents an anion.

Rigid P-chiral phosphine ligands with tert -butylmethylphosphino groups for rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes

Both enantiomers of 2,3-bis(tert-butylmethylphosphino)quinoxaline (QuinoxP*), 1,2-bis(tert-butylmethylphosphino)benzene (BenzP*), and 1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene (DioxyBenzP*) were prepared in short steps from enantiopure (S)- and (R)-tert-butylmethylphosphine-boranes as the key intermediates. All of these ligands were crystalline solids and were not readily oxidized on exposure to air. Their rhodium complexes exhibited excellent enantioselectivities and high catalytic activities in the asymmetric hydrogenation of functionalized alkenes, such as dehydroamino acid derivatives and enamides. The practical utility of these catalysts was demonstrated by the efficient preparation of several chiral pharmaceutical ingredients having an amino acid or a secondary amine component. A rhodium complex of the structurally simple ligand BenzP* was used for the mechanistic study of asymmetric hydrogenation. Low-temperature NMR studies together with DFT calculations using methyl α-acetamidocinnamate as the standard model substrate revealed new aspects of the reaction pathways and the enantioselection mechanism.

PHOSPHINE TRANSITION METAL COMPLEX, METHOD FOR PRODUCING THE SAME AND ANTITUMOR AGENT

An anticancer agent having a novel chemical structure and high anticancer activity is provided. A phosphine transition metal complex of general formula (1) and an anticancer agent containing the complex are disclosed. R1 and R2, which may be the same or different, each represent a group having 1 to 10 carbon atoms selected from a straight-chain or branched alkyl group, a cycloalkyl group, a substituted cycloalkyl group, an adamantyl group, a phenyl group, and a substituted phenyl group; R3 and R4, which may be the same or different, each represent a hydrogen atom, a straight-chain alkyl group having 1 to 6 carbon atoms or branched alkyl group having 1 to 6 carbon atoms; or R3 and R4 are taken together to form a saturated or unsaturated ring which may have a substituted group; M represents a transition metal atom selected from the group consisting of gold, copper, and silver; and X- represents an anion.

2, 3-Bis(dialkylphosphino)pyrazine derivative, process of producing the same, and metal complex having the same as ligand

An optically active 2,3-bis(dialkylphosphino)pyrazine derivative represented by formula (1) is disclosed. The pyrazine derivative is preferably a quinoxaline derivative represented by formula (2). In formula (1) and (2), R1 is preferably a t-butyl or adamantyl group, and R2 is preferably a methyl group. wherein R1 is a substituted or unsubstituted, straight chain or branched alkyl group having 2 to 10 carbon atoms; R2 is a substituted or unsubstituted, straight chain or branched alkyl group having fewer carbon atoms than R1; and R3 and R4, which may be the same or different, are each a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, or R3 and R4 are taken together to form a saturated or unsaturated ring. wherein R1 and R2 are as defined above; and R5 is a monovalent substituent.