139139-86-9 Usage
Description
(R)-H8-BINAP, also known as (R)-1,1'-Bis(diphenylphosphino)-1,1'-binaphthyl, is a diphenylphosphinobenzoic acid (DPPBA) based ligand that is widely utilized in various catalytic applications, particularly in the field of organic chemistry. It possesses a unique structure that enables high enantioselectivity in numerous chemical reactions, making it a valuable tool for the synthesis of complex molecules with specific stereochemistry.
Uses
Used in Pharmaceutical Industry:
(R)-H8-BINAP is used as a catalytic ligand for the enantioselective synthesis of various pharmaceutical compounds, such as dihydrobenzofurans and dihydronaphthofurans, which are important structural motifs in many biologically active molecules. Its application in this field is crucial for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
(R)-H8-BINAP is used as a chiral ligand in the preparation of axially chiral biaryl compounds through gold-catalyzed stereoselective intramolecular hydroarylation. These compounds are essential building blocks in the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Fine Chemicals Industry:
(R)-H8-BINAP is employed as a catalyst in the preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Br?nsted acids and palladium BINAP complexes. These indolines are valuable intermediates in the synthesis of various fine chemicals and natural products.
Used in Material Science:
(R)-H8-BINAP is used as a chiral ligand in the stereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes. These complex molecular structures are essential for the development of advanced materials with unique properties.
Used in Research and Development:
(R)-H8-BINAP is utilized as a chiral ligand in the rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes. This reaction is a powerful tool for the synthesis of complex organic molecules with multiple stereocenters, which are often found in biologically active compounds and natural products.
Used in Asymmetric Catalysis:
(R)-H8-BINAP is used as a chiral ligand in the stereoselective preparation of 2,3-substituted indolines via Pd-catalyzed hydrogenation of (α-hydroxyalkyl)indoles. These indolines are important intermediates in the synthesis of various pharmaceuticals and agrochemicals, highlighting the importance of (R)-H8-BINAP in the development of enantioselective catalysts for industrial applications.
Reaction
Biaryl bisphosphine ligand. The H8-BINAP ligand, as the ruthenium complex, catalyzes hydrogenation of unsaturated carboxylic acids to a higher ee than does BINAP.
The ruthenium catalyzed hydrogenation of aryl propenoic acid to produce the drug Ibuprofen.
Rhodium catalyzed asymmetric regioselective 1,4-addition of arylboronic acids to 3-substituted maleimides.
Ligand for palladium-catalyzed enantioselective hydrogenation of substituted indoles.
Rhodium-catalyzed enantioselective cyclization of γ-alkynylaldehydes with acyl phosphonates.
Enantioselective synthesis of axially chiral 1-arylisoquinolines by Rh-catalyzed [2+2+2] cycloaddition.
Enantioselective synthesis of 2,3-disubstituted indolines through Bronsted acid/Pd-complex-promoted tandem reactions.
Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles
Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with arylisocyanates
Asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)-indoles
Asymmetric Rh(I)-catalyzed intramolecular [3+2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter.
Enantioselective intermolecular [2+2+2] cycloadditions of ene-allenes with allenoates.
Rh-catalyzed one-pot intermolecular [2+2+2] trimerization/asymmetric intramolecular [4+2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
Rh-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides.
Check Digit Verification of cas no
The CAS Registry Mumber 139139-86-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,1,3 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 139139-86:
(8*1)+(7*3)+(6*9)+(5*1)+(4*3)+(3*9)+(2*8)+(1*6)=149
149 % 10 = 9
So 139139-86-9 is a valid CAS Registry Number.
InChI:InChI=1/C44H40P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-12,19-26,29-32H,13-18,27-28H2
139139-86-9Relevant articles and documents
NOVEL RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL COMPOUND USING SAME AS CATALYST
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Paragraph 0064, (2014/03/21)
The present invention provides: a novel ruthenium complex which has excellent catalytic activity with respect to reactivity in the reduction of a multiple bond, in particular, in the asymmetric reduction of a carbonyl compound, enantioselectivity, etc.; a catalyst which comprises the ruthenium complex; and a process for producing optically active compound, in particular, an optically active alcohol compound, using the catalyst. The ruthenium complex has a ruthenacyclic structure. The catalyst is a catalyst for asymmetric reduction which comprises the ruthenium complex.
Method for making an optically active diphosphine ligand
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, (2008/06/13)
The present invention provides a method for making compound (1) by reacting compound (2) with phosphine oxide (3) in the presence of a transition metal/phosphine complex and optionally reducing the reaction product: STR1 where n represents 0 or 1; the double line having a continuous line and a dotted line represents a double bond or a single bond such that the ring having the double line forms a naphthalene ring or an octahydronaphthalene ring with an adjacent benzene ring; Tf represents a trifluoromethanesulfonyl group; and Ar represents a phenyl group, a substituted phenyl group or a naphthyl group. The present invention provides an economical way to produce compound (1) as a ligand of a complex useful as a catalyst for a variety of asymmetric synthesis reactions.
Synthesis of Partially Hydrogenated BINAP Variants
Zhang, Xiaoyong,Mashima, Kazushi,Koyano, Kinko,Sayo, Noboru,Kumobayashi, Hidenori,et al.
, p. 7283 - 7286 (2007/10/02)
Three pairs of new axially dissymmetric diphosphine ligands, (R)-(-)- and (S)-(+)-2,2'-bis(dicyclohexylphosphino)-1,1'-binaphthyl , (R)-(+)- and (S)-(-)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphth