(4-{5-[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphanyl]-2H-1,3-benzodioxol-4-yl}-2H-1,3-benzodioxol-5-yl)bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphane

• ChemBase ID: 140818
• Molecular Formular: C74H100O8P2
• Molecular Mass: 1179.528522
• Monoisotopic Mass: 1178.68934342
• SMILES: CC(C)(C)c1cc(cc(c1OC)C(C)(C)C)P(c1ccc2c(c1c1c(ccc3c1OCO3)P(c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C)c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C)OCO2)c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C
• Canonical SMILES: COc1c(cc(cc1C(C)(C)C)P(c1ccc2c(c1c1c3OCOc3ccc1P(c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C)c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C)OCO2)c1cc(c(c(c1)C(C)(C)C)OC)C(C)(C)C)C(C)(C)C
• InChI: InChI=1S/C74H100O8P2/c1-67(2,3)47-33-43(34-48(61(47)75-25)68(4,5)6)83(44-35-49(69(7,8)9)62(76-26)50(36-44)70(10,11)12)57-31-29-55-65(81-41-79-55)59(57)60-58(32-30-56-66(60)82-42-80-56)84(45-37-51(71(13,14)15)63(77-27)52(38-45)72(16,17)18)46-39-53(73(19,20)21)64(78-28)54(40-46)74(22,23)24/h29-40H,41-42H2,1-28H3
• InChIKey: ZNORAFJUESSLTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-{5-[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphanyl]-2H-1,3-benzodioxol-4-yl}-2H-1,3-benzodioxol-5-yl)bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphane
• IUPAC Traditional name: (4-{5-[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphanyl]-2H-1,3-benzodioxol-4-yl}-2H-1,3-benzodioxol-5-yl)bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphane
• Synonyms: (S)-(+)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole; (S)-DTBM-SEGPHOS®; (R)-(-)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole; [(4R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine]; (R)-DTBM-SEGPHOS®; (S)-(+)-5,5′-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4′-二-1,3-苯并二噁茂; (R)-(-)-5,5′-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4′-二-1,3-苯并二噁茂; [(4R)-(4,4′-二-1,3-苯并二噁茂)-5,5′-二基]二[双(3,5--二叔丁基-4-甲氧基苯基)膦]

Database IDs

• CAS Number: 210169-40-7; 566940-03-2
• MDL Number: MFCD09753003
• PubChem SID: 162235058
• PubChem CID: 11194192

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 21.2264
• LogD (pH = 7.4): 21.2264
• Log P: 21.2264
• Molar Refractivity: 349.0378 cm^3
• Polarizability: 138.4536 Å^3
• Polar Surface Area: 73.84 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥94%
• Empirical Formula (Hill Notation): C74H100O8P2

DETAILS

Sigma Aldrich - 692484

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Catalyst involved in:
• [3,3]-Sigmatropic rearrangements using cyclopropane probes
• Asymmetric intramolecular hydroacylation of ketoaldehydesReactant involved in:
• The synthesis of gold-diphosphine complexes for use as catalysts
• Cycloaddition of allenenes to yield alkylidenecyclobutanes

Sigma Aldrich - 692980

Packaging
1 g in glass bottle
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Catalytic ligand for:
• Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
• Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
• Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
• Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
• Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition