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104762-38-1

(S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE, with the molecular formula C23H21O2P, is a phospholane compound that plays a significant role in the field of organic chemistry. It is widely recognized for its ability to act as a ligand in various organic synthesis and catalysis processes, including asymmetric hydrogenation, cross-coupling reactions, and asymmetric allylation. (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE's unique structure allows it to selectively control the stereochemistry of certain reactions, making it a valuable tool for chemists and researchers.

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  • 104762-38-1 Structure

  • Basic information

    1. Product Name: (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE
    2. Synonyms: (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE
    3. CAS NO:104762-38-1
    4. Molecular Formula: C21H21O2P
    5. Molecular Weight: 336.364001
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 104762-38-1.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE(CAS DataBase Reference)
    10. NIST Chemistry Reference: (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE(104762-38-1)
    11. EPA Substance Registry System: (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE(104762-38-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 104762-38-1(Hazardous Substances Data)

104762-38-1 Usage

Uses

Used in Organic Synthesis:
(S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE is used as a ligand in organic synthesis for its ability to selectively control the stereochemistry of reactions. This selective control is crucial in obtaining desired products with specific stereochemical configurations, which is essential in the development of pharmaceuticals and other complex organic molecules.
Used in Catalysis:
In the field of catalysis, (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE serves as a ligand to enhance the efficiency and selectivity of various chemical reactions. Its use in catalysis can lead to improved reaction rates, reduced side products, and increased yields, making it a valuable asset in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
(S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE is used as a key component in the synthesis of various pharmaceutical compounds. Its ability to control stereochemistry and participate in complex organic reactions makes it an essential tool in the development of new drugs and therapeutic agents.
Used in Asymmetric Hydrogenation:
In the chemical process of asymmetric hydrogenation, (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE is used as a ligand to achieve high enantioselectivity and stereospecificity. This is particularly important in the production of chiral compounds, which often have different biological activities and are crucial in the pharmaceutical industry.
Used in Cross-Coupling Reactions:
(S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE is utilized as a ligand in cross-coupling reactions, which are essential for the formation of carbon-carbon bonds in organic synthesis. Its use in these reactions can lead to the creation of complex molecular structures with high selectivity and efficiency.
Used in Asymmetric Allylation:
As a ligand in asymmetric allylation reactions, (S)-4-METHYL-2,2,2-TRIPHENYL-2LAMBDA5-[1,3,2]DIOXAPHOSPHOLANE contributes to the formation of carbon-carbon bonds with high stereoselectivity. This is particularly important in the synthesis of biologically active molecules and the development of new pharmaceuticals.

Check Digit Verification of cas no

The CAS Registry Mumber 104762-38-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,7,6 and 2 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 104762-38:
(8*1)+(7*0)+(6*4)+(5*7)+(4*6)+(3*2)+(2*3)+(1*8)=111
111 % 10 = 1
So 104762-38-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H21O2P/c1-18-17-22-24(23-18,19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-16,18H,17H2,1H3/t18-/m0/s1

104762-38-1Relevant articles and documents

Highly Regioselective and Stereospecific Functionalization of 1,2-Proanediol with Trimethyl(X)silanes Employing the 1,3,2λ5-Dioxaphospholane Methodology

Mathieu-Pelta, Isabel,Evans, Slayton A.

, p. 3409 - 3413 (2007/10/02)

The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2λ5-dioxaphospholanes (2) was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br; Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts.A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominatly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).

The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology

Pautard-Cooper, Anne,Evans Jr., Slayton A.,Kenan Jr., William Rand

, p. 1603 - 1610 (2007/12/18)

Stereo specific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2λ5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either P-toluenesulfonic acid (P-TsOH) in tetrahydrofuran solvent or P-TsOH/sodium azide in acetonitrile solvent, respectively.

Lewis Acid Promoted Decomposition of Substituted 1,3,2λ5-Dioxaphospholanes: Kinetic and Thermodynamic Studies

Murray, William T.,Evans, Slayton A.

, p. 2440 - 2446 (2007/10/02)

The kinetics of Lewis acid mediated decomposition of a series of substituted 1,3,2λ5-dioxaphospholanes, prepared by transphosphoranylation of 1,2-diols with diethoxytriphenylphosphorane (DTPP), is reported.The rate data obtained from 31P NMR spectroscopic measurements, emphasize the influence of (i) variations in the coordination potential (i.e., cationic charge) of the Lewis acids, (ii) methyl group substitution at C-4 and C-5 in the 1,3,2λ5-dioxaphospholanyl substructure, and (iii) changes in solvent polarity.Also, the propensity for 1,2-hydride migratory processes attending conformationally restricted bicyclic 1,3,2λ5-dioxap hospholanes versus epoxide formation from the collapse of simple cyclic 1,3,2λ5-dioxaphospholanes were examined.The results are best explained by invoking a "site-selective" coordination by the catalyst to one of the "ethereal" oxygens within 1,3,2λ5-dioxaphospholanyl moiety initiating P-O bond cleavage and ultimately affording the requisite betaine intermediate(s).Methyl substitution on the 1,3,2λ5-dioxaphospholanyl hydrocarbon backbone decreases the rate of P-O bond cleavage, and the 1,2-hydride migratory process within conformationally rigid bicyclic 1,3,2λ5-dioxaphospholanes requires ca. 2.0 kcal/mol more energy than the decomposition of the monocyclic 1,3,2λ5-dioxaphospholanes via 3-exo-tet cyclization to the respective cyclic ethers.Mechanistic implications of various reactions are discussed.

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