Cas no 158923-11-6 ((R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine)

(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine is a chiral bidentate phosphine ligand featuring a ferrocene backbone with dicyclohexylphosphine and di-tert-butylphosphine substituents. Its rigid, sterically demanding structure enhances enantioselectivity in asymmetric catalysis, particularly in transition-metal-catalyzed reactions such as hydrogenations, cross-couplings, and C–C bond formations. The electron-rich tert-butyl groups improve steric control, while the ferrocenyl scaffold ensures stability under harsh conditions. This ligand is valued for its high catalytic efficiency and selectivity in producing enantiomerically pure compounds, making it a preferred choice in pharmaceutical and fine chemical synthesis. Its air-stable nature further simplifies handling and storage compared to more sensitive phosphine ligands.
(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine structure
158923-11-6 structure
Product Name:(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine
CAS No:158923-11-6
MF:C32H52FeP2
MW:554.547812461853
MDL:MFCD03426994
CID:109043
PubChem ID:24889121
Update Time:2025-05-20

(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine Chemical and Physical Properties

Names and Identifiers

    • Ferrocene,1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-,(2R)-
    • (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine
    • [(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]di-tert-butylphosphine
    • (R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine
    • (R)-(S)-cy2PF-PtBu2
    • (R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyli-tert-butylphosphine
    • (r,r)-1-[1-(di-tert-butylphosphino)ethyl]-2-(dicyclohexylphosphino)ferrocene (acc to )
    • [(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine
    • 1-[2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine
    • 1-dicyclohexylphosphino-2-di-t-butylphosphinoethylferrocene
    • Josiphos ligand
    • JOSIPHOS SL-J009-1
    • (Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine
    • (R)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE
    • (R,R)-1-[1-(DI-TERT-BUTYLPHOSPHINO)ETHYL]-2-(DICYCLOHEXYLPHOSPHINO)FERROCENE
    • Josiphos SL-J009-1 / (R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyli-tert-butylphosphine
    • (R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine >=97%
    • (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine,min.97%
    • (R)-1-[(S)-2-(Dicyclohexylphosphino) ferrocenyl]ethyli-tert-butylphosphine
    • (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl] ethyldi-t-butylphosphine, min. 97%
    • (R)-1-[(Sp)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl di-tert-butylphosphine
    • (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine
    • MDL: MFCD03426994
    • Inchi: 1S/C27H47P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h14,19-23H,8-13,15-18H2,1-7H3;1-5H;/t21-;;/m1../s1
    • InChI Key: FFFWTQLOUUWUJJ-GHVWMZMZSA-N
    • SMILES: [Fe].[CH]1[CH][CH][C](P(C2CCCCC2)C2CCCCC2)[C]1[C@H](P(C(C)(C)C)C(C)(C)C)C.[CH]1[CH][CH][CH][CH]1

Computed Properties

  • Exact Mass: 554.28900
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 35
  • Rotatable Bond Count: 7
  • Complexity: 467
  • Covalently-Bonded Unit Count: 3
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Melting Point: 118-120oC
  • Solubility: 可溶于氯仿(輕微)、甲醇(非常輕微)
  • PSA: 27.18000
  • LogP: 10.06670
  • Specific Rotation: -185° ±10° (c 0.5, CHCl3)

(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine Security Information

  • Signal Word:Warning
  • Hazard Statement: H302-H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Safety Instruction: S22-S24/25
  • Safety Term:S22-24/25
  • Storage Condition:Inert atmosphere,2-8°C

(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine Customs Data

  • HS CODE:29319090

(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine Pricemore >>

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(R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine Related Literature

Additional information on (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine

Introduction to (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine and Its Applications in Modern Chemical Biology

The compound with the CAS number 158923-11-6 is a highly specialized organometallic phosphine derivative, formally known as (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine. This intricate molecular structure combines the unique properties of ferrocene, dicyclohexylphosphino, and di-tert-butylphosphine moieties, making it a versatile and valuable reagent in the field of synthetic chemistry and pharmaceutical research.

At the core of this compound's functionality lies its chiral center, which is crucial for applications in asymmetric synthesis. The (R)-configuration ensures that the compound exhibits specific stereoselectivity, a key factor in the development of enantiomerically pure pharmaceuticals. This characteristic has garnered significant attention in recent years, particularly in the context of drug discovery where enantiomeric purity can significantly impact a drug's efficacy and safety profile.

The ferrocene moiety in (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine contributes to its unique electronic properties. Ferrocene-based compounds are well-known for their stability and ability to participate in various catalytic processes. This makes them particularly useful in transition metal-catalyzed reactions, where they can act as ligands or catalysts themselves. The dicyclohexylphosphino group further enhances the compound's ability to coordinate with transition metals, facilitating a wide range of synthetic transformations.

In recent years, there has been a surge in research focused on developing novel phosphine-based ligands for asymmetric catalysis. The di-tert-butylphosphine component of this compound provides steric hindrance, which is essential for controlling the selectivity of catalytic reactions. This steric effect is particularly important in cross-coupling reactions, where it helps to prevent unwanted side reactions and ensures high yields of the desired product.

One of the most exciting applications of (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine is in the field of pharmaceutical synthesis. Researchers have leveraged its chiral properties to develop novel intermediates for complex drug molecules. For instance, studies have demonstrated its utility in the synthesis of beta-blockers and antiviral agents, where enantiomeric purity is critical for therapeutic efficacy. The compound's ability to facilitate highly selective reactions has also made it a valuable tool in the development of protease inhibitors, which are essential for treating various diseases.

The role of this compound in medicinal chemistry extends beyond mere reactivity. Its stability under various reaction conditions makes it an ideal candidate for large-scale synthesis. Additionally, its compatibility with green chemistry principles—such as reduced solvent usage and minimal waste generation—aligns well with contemporary environmental concerns. These attributes have positioned (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine as a cornerstone in modern pharmaceutical research.

Recent advancements in computational chemistry have further highlighted the potential of this compound. Molecular modeling studies have revealed insights into its binding interactions with transition metals, providing a deeper understanding of its catalytic mechanism. These insights have not only enhanced our theoretical knowledge but also guided experimental design, leading to more efficient synthetic strategies.

The versatility of (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine is also evident in its application as a building block for more complex molecular architectures. Chemists have utilized its unique reactivity to construct polycyclic systems and heterocycles, which are prevalent motifs in many biologically active compounds. This capability underscores its importance as a synthetic intermediate and highlights its potential for future drug development.

In conclusion, (R)-1-(SP)-2-(Dicyclohexylphosphino)ferrocenylethyldi-tert-butylphosphine (CAS no. 158923-11-6) represents a significant advancement in organometallic chemistry and pharmaceutical research. Its chiral nature, combined with its ability to participate in diverse catalytic processes, makes it an indispensable tool for synthetic chemists. As research continues to uncover new applications for this compound, its impact on drug discovery and development is poised to grow even further.

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