CAS 14187-32-7|6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecene|2,3,11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene|dibenzo-18-crown-6|2,5,8,15,18,21-hex...

General Information

Structure

Molecular Formula

C₂₀H₂₄O₆

Molecular Mass

360.40096

Exact Mass

360.15728849

Charge

InChI

InChI=1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2

InChIKey

YSSSPARMOAYJTE-UHFFFAOYSA-N

Canonic Smiles

O1CCOc2ccccc2OCCOCCOc2c(OCC1)cccc2

Isomeric Smiles

O1c2c(cccc2)OCCOCCOc2c(cccc2)OCCOCC1

Calculated Properties

JChem

LogD (pH = 7.4)

2.88

LogD (pH = 5.5)

2.88

Log P

2.88

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-3.73

Polar Surface Area

55.38

Polarizability

39.19

Molar Refractivity

96.12

LOG S

-4.01

Data Source

Names and Identifiers

Synonyms

6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecene2,3,11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dieneDIBENZO-18-CROWN-66,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecineDibenzo-18-crown-6-ether二苯并-18-冠醚-62,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八-2,11-二烯锡(II) 离子载体 ITin(II) ionophore I二苯并-18-冠醚-6Dibenzo-18-crown-66,7,9,10,17,18,20,21-八氢二苯并[b,k][1,4,7,10,13,16]六氧杂环十八碳烯Dibenzo-18-crown-62,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene二苯并-18-冠-6醚dibenzo-18-crown-6DB18C6dicyclohexano-18-crown-6dibenzo-18-crown-6-etherDibenzo-18-crown-62,3:11,12-dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine

IUPAC Traditional name

dibenzo-18-crown-6 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0⁹,¹⁴]hexacosa-1(22),9(14),10,12,23,25-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(26),9,11,13,22,24-hexaene

IUPAC name

2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(26),9,11,13,22,24-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0⁹,¹⁴]hexacosa-1(22),9(14),10,12,23,25-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0⁹,¹⁴]hexacosa-1(26),9,11,13,22,24-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0⁹,¹⁴]hexacosa-1(22),9,11,13,23,25-hexaene 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0⁹,¹⁴]hexacosa-1(26),9,11,13,22,24-hexaene

Names and Identifiers

Registration numbers

MDL Number

EC Number

Merck Index

Beilstein Number

CAS Number

PubChem SID

248497321620400192486030387351119

KEGG ID

CHEMBL

Chemspider ID

PubChem CID

Wikipedia Title

CHEBI ID

358732CHEBI:358732CHEBI:34685

PubMed Citation Links

32255649188111311932689724046607232475741769077029582664284775132096115522873431285055666220152315259763361060517300184336726321777457627624839283979172120119933356146

SureChEMBL Database

SCHEMBL35765

CompTox Database

DTXSID6022428

MetaboLights Database

LINCS Database

Gmelin ID

ACToR Database

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150847

Off-white to gray crystals.
A crown ether that acts as a complexing agent which solubilizes alkali metal ions in non-polar solvents.

Wikipedia

Dibenzo-18-crown-6

Sigma Aldrich

158399

Application
Phase-transfer catalyst employed in monoazaporphyrin syntheses.1 Agent used for ion transfer across membranes2 and as a synthon for preparation of liquid crystal polyesters.3
Packaging
2.5, 10, 50 g in glass bottle

33531

Other Notes
Macrocyclic complexing agent for cations1

49902

General description
Visit our Sensor Applications portal to learn more.
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

ChEBI

CHEBI:358732

A crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18.

Molecule Details

References

PubChem Literature

From Data Sources

• Comparison of the rates of displacement of F^- in 1-fluoro-2- or 4-nitrobenzene with KOMe and KO-t-Bu in the presence of this crown ether gave a result (t-BuO^- >> MeO^-) opposite to the pattern observed in its absence: J. Chem. Soc., Perkin 2, 55 (1973).

• In combination with Benzyltriethylammonium chloride, A13268, promotes the oxidative decarboxylation of arylacetic acids with NaIO₄ to give high yields of the aryl aldehydes: Indian J. Chem. B, 35B, 151 (1996). Under the same conditions, phenacyl bromides are converted to benzoic acids.

• Catalyst for the halogenative cleavage of epoxides with Br₂ or I₂, giving halohydrins in high yields: J. Org. Chem., 63, 1455 (1998).

• Promotes the generation of bromochlorocarbene from Chlorodibromomethane, A16938: Syntheis, 783 (1977); Tetrahedron, 33, 363 (1977), and of dibromocarbene from Bromoform, A11904: Org. Synth., 75, 98 (1997).

• See also 18-Crown-6, A11249 and Appendix 2.

• Catalyst for the formation of phenacyl esters from phenacyl bromides and K salts of carboxylic acids in acetonitrile: Synth. Commun., 26, 1747 (1996).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

IUPAC name

Registration numbers

MDL Number

EC Number

Merck Index

Beilstein Number

CAS Number

PubChem SID

248497321620400192486030387351119

KEGG ID

CHEMBL

Chemspider ID

PubChem CID

Wikipedia Title

CHEBI ID

358732CHEBI:358732CHEBI:34685

PubMed Citation Links

32255649188111311932689724046607232475741769077029582664284775132096115522873431285055666220152315259763361060517300184336726321777457627624839283979172120119933356146

SureChEMBL Database

SCHEMBL35765

CompTox Database

DTXSID6022428

MetaboLights Database

LINCS Database

Gmelin ID

ACToR Database

Molecule Details

Off-white to gray crystals.
A crown ether that acts as a complexing agent which solubilizes alkali metal ions in non-polar solvents.

Wikipedia

Dibenzo-18-crown-6

Sigma Aldrich

158399

33531

Other Notes
Macrocyclic complexing agent for cations1

49902

General description
Visit our Sensor Applications portal to learn more.
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

ChEBI

CHEBI:358732

A crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18.

References

PubChem Literature

From Data Sources

• Catalyst for the halogenative cleavage of epoxides with Br₂ or I₂, giving halohydrins in high yields: J. Org. Chem., 63, 1455 (1998).

• See also 18-Crown-6, A11249 and Appendix 2.

• Catalyst for the formation of phenacyl esters from phenacyl bromides and K salts of carboxylic acids in acetonitrile: Synth. Commun., 26, 1747 (1996).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:75101