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486429-99-6 molecular structure
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[17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.02,7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane

ChemBase ID: 141656
Molecular Formular: C39H32O2P2
Molecular Mass: 594.617702
Monoisotopic Mass: 594.18775352
SMILES and InChIs

SMILES:
c1ccc(cc1)P(c1ccccc1)c1cccc2c1c1c(cccc1P(c1ccccc1)c1ccccc1)OCCCO2
Canonical SMILES:
C1COc2cccc(c2c2c(OC1)cccc2P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C39H32O2P2/c1-5-16-30(17-6-1)42(31-18-7-2-8-19-31)36-26-13-24-34-38(36)39-35(41-29-15-28-40-34)25-14-27-37(39)43(32-20-9-3-10-21-32)33-22-11-4-12-23-33/h1-14,16-27H,15,28-29H2
InChIKey:
GTIXSUJKFAATAE-UHFFFAOYSA-N

Cite this record

CBID:141656 http://www.chembase.cn/molecule-141656.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.02,7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane
IUPAC Traditional name
[17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.02,7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane
Synonyms
(S)-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin
(S)-C3-TunePhos
(R)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin
(R)-C3-TunePhos
(S)-二(二苯基膦基)-7,8-二氢-6H-二苯并[f,h][1,5]二噁壬英
(R)-(-)-1,13-二(二苯基膦)-7,8-二氢-6H-二苯并[f,h][1,5]二氧杂环壬四烯
CAS Number
486429-99-6
301847-89-2
MDL Number
MFCD06658115
PubChem SID
24883784
162235890
PubChem CID
10722198

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 10722198 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 9.2199  LogD (pH = 7.4) 9.2199 
Log P 9.2199  Molar Refractivity 178.1468 cm3
Polarizability 71.39727 Å3 Polar Surface Area 18.46 Å2
Rotatable Bonds Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
153-161 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -252±5°, c = 1 in chloroform expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Empirical Formula (Hill Notation)
C39H32O2P2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 650862 external link
Application
Provides comparable or superior enantioselectivities and catalytic abilities to BINAP in Ru-catalyzed asymmetric hydrogenations of β-keto esters,6 cyclic β-(acylamino)acrylates7 and α-phthalimide ketones.8
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationLigand used in:
• Redox-neutral domino reaction of arylethynylbenzylidenearylpentynones catalyzed by gold catalyst1
• Asymmetric allylic O-alkylation2
• Asymmetric alkylation of racemic secondary phosphines catalyzed by ruthenium chiral diphosphine hydride complexes3
• Stereoselective preparation of cyclopropylcarboxaldehydes via Rh-catalyzed asymmetric hydroformylation of cyclopropenes4
• Rhodium-catalyzed asymmetric hydrogenations5
Packaging
100, 500 mg in glass bottle
Sigma Aldrich - 696064 external link
Application
Provides comparable or superior enantioselectivities and catalytic abilities to BINAP in Ru-catalyzed asymmetric hydrogenations of β-keto esters5, cyclic β-(acylamino)acrylates6 and a-phthalimide ketones7.
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationReactant for:
• Asymmetric hydrogenation of ketones with TunePhos/diamine/ruthenium complexes1
• Stereoselective preparation of arylalkyl esters via enantioselective hydrogenation of enol acetates2Precatalyst for:
• Enantioselective iridium-catalyzed carbonyl allylation from alcohol or aldehyde by transfer hydrogenative coupling of allyl acetate3Catalyst for:
• Enantioselective hydrogenation of a-keto esters to a-hydroxy esters using Ru-tunephos catalysts4
Packaging
100, 500 mg in glass bottle

REFERENCES

REFERENCES

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PATENTS

PATENTS

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