Cas no 871130-17-5 (Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-)

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- structure
871130-17-5 structure
Product Name:Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-
CAS No:871130-17-5
MF:C40H25O4P
MW:600.597871541977
CID:719272
PubChem ID:329760854
Update Time:2025-07-15

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Chemical and Physical Properties

Names and Identifiers

    • Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-
    • (R)-(-)-VAPOL hydrogenphosphate
    • S-Vapol Hydrogenphosphate
    • (S)-Vapol hydrogen phosphate
    • 17-hydroxy-3,31-diphenyl-16,18-dioxa-17??-phosphaheptacyclo[17.12.0.0(2),(1)?.0?,(1)?.0?,(1)(3).0(2)?,(2)?.0(2)(1),(2)?]hentriaconta-1(19),2(15),3,5(14),6,8(13),9,11,20(29),21(26),22,24,27,30-tetradecaen-17-one
    • 175223-69-5
    • (R)-()-VAPOL hydrogenphosphate
    • CHEMBL1331448
    • (S)-18-HYDROXY-8,9-DIPHENYL-DIPHENANTHRO[4,3-D:3',4'-F][1,3,2]DIOXAPHOSPHEPIN-18-OXIDE
    • (8aR)-18-Hydroxy-8,9-diphenyldiphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepine 18-oxide
    • 871130-18-6
    • NCGC00161029-02
    • (8aR)-18-Hydroxy-8,9-diphenyl-18-oxide-diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin
    • J-502298
    • (8aS)-18-Hydroxy-8,9-diphenyl-18-oxide-diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin
    • (S)-VAPOL hydrogenphosphate
    • CS-B0722
    • 18-hydroxy-8,9-diphenyldiphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepine 18-oxide
    • SCHEMBL13156447
    • (R)-VAPOL HYDROGENPHOSPHATE
    • NCGC00161029-01
    • 871130-17-5
    • D97479
    • MFCD09265084
    • (8aS)-18-Hydroxy-8,9-diphenyldiphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepine 18-oxide
    • 17-hydroxy-3,31-diphenyl-16,18-dioxa-17lambda5-phosphaheptacyclo[17.12.0.02,15.05,14.08,13.020,29.021,26]hentriaconta-1(31),2,4,6,8,10,12,14,19,21,23,25,27,29-tetradecaene 17-oxide
    • (R)-( C)-VAPOL hydrogenphosphate
    • MDL: MFCD09265084
    • Inchi: 1S/C40H25O4P/c41-45(42)43-39-35-29(21-19-27-15-7-9-17-31(27)35)23-33(25-11-3-1-4-12-25)37(39)38-34(26-13-5-2-6-14-26)24-30-22-20-28-16-8-10-18-32(28)36(30)40(38)44-45/h1-24H,(H,41,42)
    • InChI Key: YKIJNEDTUDPMNC-UHFFFAOYSA-N
    • SMILES: O=P1(OC2C3C4C(=CC=CC=4)C=CC=3C=C(C=2C2C(=C3C4C(=CC=CC=4)C=CC3=CC=2C2C=CC=CC=2)O1)C1C=CC=CC=1)O

Computed Properties

  • Exact Mass: 600.14904627g/mol
  • Monoisotopic Mass: 600.14904627g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 45
  • Rotatable Bond Count: 2
  • Complexity: 1000
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 10.6
  • Topological Polar Surface Area: 55.8?2

Experimental Properties

  • Melting Point: >400?°C
  • PSA: 65.57000
  • LogP: 11.17200
  • Optical Activity: [α]22/D +412°, c =?1 in chloroform

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Pricemore >>

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(8aS)-18-Hydroxy-8,9-diphenyl-18-oxide-diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin, 98%, (99% ee); .
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Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Pyridine ,  Phosphorus oxychloride Solvents: Pyridine ;  25 °C; 6 h, 25 °C
1.2 Reagents: Water ;  25 °C; 2 h, 25 °C
Reference
New derivatives of VAPOL and VANOL: structurally distinct vaulted chiral ligands and Bronsted acid catalysts
Desai, Aman A.; et al, Synthesis, 2010, (21), 3670-3680

Production Method 2

Reaction Conditions
Reference
Bronsted acid-catalyzed imine amidation
Rowland, Gerald B.; et al, Journal of the American Chemical Society, 2005, 127(45), 15696-15697

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Raw materials

Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- Preparation Products

Additional information on Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-

Recent Advances in the Study of Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- (CAS: 871130-17-5)

The compound Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- (CAS: 871130-17-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This heterocyclic phosphorus-containing molecule exhibits unique structural and electronic properties, making it a promising candidate for various applications, including catalysis, material science, and drug development. Recent studies have focused on elucidating its synthesis, reactivity, and potential biological activities.

One of the key breakthroughs in the synthesis of this compound involves the use of stereoselective methods to achieve the (8aS)- configuration, which is critical for its biological activity. Researchers have optimized reaction conditions to improve yield and purity, leveraging advanced spectroscopic techniques such as NMR and X-ray crystallography for structural confirmation. The compound's stability under physiological conditions has also been investigated, providing insights into its potential as a therapeutic agent.

In terms of biological activity, preliminary studies suggest that Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin derivatives exhibit inhibitory effects on specific enzymes involved in inflammatory pathways. For instance, in vitro assays have demonstrated its ability to modulate the activity of phosphodiesterases (PDEs), which are implicated in various diseases, including cancer and neurodegenerative disorders. These findings highlight the compound's potential as a lead structure for the development of novel PDE inhibitors.

Further research has explored the compound's mechanism of action at the molecular level. Computational modeling and molecular docking studies have revealed its high affinity for the active sites of target enzymes, providing a rationale for its observed bioactivity. Additionally, structure-activity relationship (SAR) studies have identified key functional groups that contribute to its potency and selectivity, offering valuable guidance for future medicinal chemistry efforts.

Despite these promising results, challenges remain in translating these findings into clinical applications. Issues such as bioavailability, metabolic stability, and potential toxicity need to be addressed through comprehensive preclinical studies. Recent efforts have focused on derivatization strategies to enhance the compound's pharmacokinetic properties while maintaining its therapeutic efficacy.

In conclusion, Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)- represents a fascinating area of research with significant potential for drug discovery and development. Continued interdisciplinary collaboration between chemists, biologists, and pharmacologists will be essential to unlock its full therapeutic potential and address the remaining challenges in its development.

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