“Phanephos”的意思、由来-开放百科全书

词条

Phanephos

释义

Preparation
Uses
References

{{Chembox
| ImageFile = Diphosphino phanephos.png
| ImageSize = 150px
| IUPACName = (S)-(+)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane; (R)-(−)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane
| OtherNames = (S)-Phanephos; (R)-Phanephos
|Section1={{Chembox Identifiers
| CASNo = 364732-88-7
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Comment = (R)
| CASNo1 = 192463-40-4
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1_Comment = (S)
| PubChem =
| ChemSpiderID = 9040059
| SMILES = C1CC2=C(C=C(CCC3=C(C=C1C=C3)P(C4=CC=CC=C4)C5=CC=CC=C5)C=C2)P(C6=CC=CC=C6)C7=CC=CC=C7
| InChI = 1/C40H34P2/c1-5-13-35(14-6-1)41(36-15-7-2-8-16-36)39-29-31-21-25-33(39)27-23-32-22-26-34(28-24-31)40(30-32)42(37-17-9-3-10-18-37)38-19-11-4-12-20-38/h1-22,25-26,29-30H,23-24,27-28H2
| InChIKey = GYZZZILPVUYAFJ-UHFFFAOYAH
| StdInChI = 1S/C40H34P2/c1-5-13-35(14-6-1)41(36-15-7-2-8-16-36)39-29-31-21-25-33(39)27-23-32-22-26-34(28-24-31)40(30-32)42(37-17-9-3-10-18-37)38-19-11-4-12-20-38/h1-22,25-26,29-30H,23-24,27-28H2
| StdInChIKey = GYZZZILPVUYAFJ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=40 | H=34 | P=2
| Appearance = White to off-white powder or crystals
| Density =
| MeltingPtC = 222 to 225
| MeltingPt_notes =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Phanephos is an organophosphorus compound with the chemical formula (C₂H₄)₂(C₆H₃PPh₂)₂ (Ph = C₆H₅). It is a white solid that is soluble in organic solvents. It is an example of a chiral C₂-symmetric diphosphine ligand used in asymmetric hydrogenation. Many substituents have been introduced in place of the phenyl groups, e.g., i-Pr, C₆H₁₁, etc and a variety of chiral diphosphine ligands have been reported in asymmetric catalysis since the 1960s.

Preparation

Phanephos can be prepared in two steps from [2.2]paracyclophane. In the first step, [2.2]paracyclophane is dibrominated to give a pseudo-para dibromide. Thermal isomerisation then gives pseudo-ortho atropisomer of the dibromide. This isomer is subjected to lithium-halogen exchange by nBuLi and the resulting dilithium compound is treated with PPh₂Cl to give a racemic mixture of Phanephos.^[1]

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Uses

Phanephos has been used in rhodium- and ruthenium- mediated stereoselective hydrogenation of dehydro amino acid methyl esters and asymmetric reduction of various β-ketoesters with about 90 % ee.^[2]

References

1. ^Gareth J. R, Planar Chiral Phosphines Derived from [2.2]Paracyclophane , Israel Journal of Chemistry, 2012, 52. 60-75, {{DOI| 10.1002/ijch.201100098}}
2. ^R. Gleiter, H. Hopf, Modern Cyclophane Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, 2005, p.449-451 {{DOI| 10.1002/3527603964}}

4 : Chelating agents|Bisphosphanes|Phenyl compounds|Cyclophanes

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