CAS 76189-56-5|CAS 98327-87-8|CAS 76189-55-4|{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane|2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl|{1-[2-(diphenylphosphanyl)naphtha...

基本信息

化学结构

分子式

C₄₄H₃₂P₂

分子量

622.672402

精确质量

622.19792428

电荷

InChI

InChI=1S/C44H32P2/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/h1-32H

InChIKey

MUALRAIOVNYAIW-UHFFFAOYSA-N

Canonic Smiles

c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1

Isomeric Smiles

c1(c(ccc2ccccc12)P(c1ccccc1)c1ccccc1)c1c(ccc2ccccc12)P(c1ccccc1)c1ccccc1

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

11.8554

LogD (pH = 7.4)

11.8554

Log P

11.8554

摩尔折射率

195.2244

极化性

80.66715

极化表面积

0.0

可自由旋转的化学键

里宾斯基五规则

false

数据来源

名称和标识

IUPAC标准名

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane

别名

2,2'-Bis(diphenylphosphino)-1,1'-binaphthylrac-BINAP(+/-)-2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl 98%(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl[1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine](R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthaleneBINAP(R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘(R)-BINAP(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl(S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘(S)-(-)-BINAP(R)-(+)-BINAP2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(±)-BINAPBINAP(S)-(-)-1,1′-联萘-2,2'-双二苯膦(S)-BINAP(±)-2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-(1,1′-联萘-2,2′-二基)双(二苯膦)(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(S)-(-)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(±)-2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘(+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine)(±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]1,1'-[(1S)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(双二苯基磷)-1,1'-双萘(+/-)-BINAP(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene1,1'-[(1R)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine(+/-)-2,2'-双(二苯基膦基)-1,1'-联萘(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-BINAP(+)-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine](S)-BINAP(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene

IUPAC传统名

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane binap

名称和标识

数据登录号

MDL号

MFCD00010805

Beilstein号

532144349140635321444

PubChem SID

162035209248578142485047524848869248488702485781524871738

PubChem CID

634876

CAS号

76189-56-598327-87-876189-55-4

默克索引号

EC号

Chemspider ID

维基百科标题

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

Apollo Scientific

OR18264

Racemic mixture

Wikipedia

BINAP

Sigma Aldrich

693065

包装
100, 500 mg in glass bottle
Legal Information
与 Takasago 联合销售，仅供研究使用。
Application
Takasago Ligands and Complexes for Asymmetric Reactions

693057

包装
100, 500 mg in glass bottle
Legal Information
与 Takasago 联合销售，仅供研究使用。
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

295817

包装
1, 5 g in glass bottle
250 mg in glass bottle
Application
过渡金属催化不对称反应（包括氢化1和二甲硅烷基化）的有效配体。22,2′-双(二苯基膦)-1,1′-联萘及其铑和钌衍生物可作为高选择性均相催化剂，用于芳基酮、3β-酮酸酯4和 α-氨基酮的还原反应。5也可用于烯烃的不对称氢化6和氢甲酰化反应、7不对称 Heck 反应8和烯丙基的不对称异构化反应。9,10 其 Ag(I) 络合物可用于催化三氯乙酸链烯酯和醛之间的不对称羟醛反应。11其 Ag(I) 络合物也可用于催化偶氮化合物的不对称非均相 Diels-Alder 反应。12

295825

包装
1, 5 g in glass bottle
250 mg in glass bottle
Application
2,2′-双(二苯基膦)-1,1′-联萘及其铑和钌衍生物可作为高选择性均相催化剂，用于芳基酮、1β-酮酸酯2和 α-氨基酮的还原反应。3也可用于烯烃的不对称氢化4和氢甲酰化反应、5不对称 Heck 反应6和烯丙基的不对称异构化反应。7,8 用于钯催化不对称串联 Heck 反应的配体，这种碳负离子捕获过程可合成三环倍半萜烯。也可用于钌催化的 α,β-不饱和酸的不对称氢化反应。
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

481084

Application
钯催化芳基胺偶联反应的配体，用于制备去甲基硫代秋水仙碱。1可与 Cu(II) 联合使用催化芳基磺酰胺加成反应生成苯乙烯和烯烃。2亦可用于钯催化的三联吡啶胺化反应。3
General description
外消旋型 BINAP。4
包装
5, 25, 100 g in glass bottle

14798

Application
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation1
• Syntehsis of organophophine oxides as anittumor agents2
• SN2 halogenation of hydroxy groups3
• Synthesis of BINAP complexes4,5
• Studies of conformational flexibility of BINAP chelates6

14797

Other Notes
手性阻旋异构双膦；铑和钌络合物可用于不对称氢化和异构化反应1,2,3；制备 BINAP-二羧酸钌络合物4

TRC

B386851

Chiral ligand for metal mediated asymmetric catalysis.

B386850

Chiral ligand for metal mediated asymmetric catalysis.

描述信息

参考文献

PubChem文献

数据源提供

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2009)

• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)

• Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ?-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).

• Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).

• See also previous entry.

• The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).

• For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane

别名

IUPAC传统名

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane binap

数据登录号

MDL号

MFCD00010805

Beilstein号

532144349140635321444

PubChem SID

162035209248578142485047524848869248488702485781524871738

PubChem CID

634876

CAS号

76189-56-598327-87-876189-55-4

默克索引号

EC号

Chemspider ID

维基百科标题

化合物性质

描述信息

Apollo Scientific

OR18264

Racemic mixture

Wikipedia

BINAP

Sigma Aldrich

693065

包装
100, 500 mg in glass bottle
Legal Information
与 Takasago 联合销售，仅供研究使用。
Application
Takasago Ligands and Complexes for Asymmetric Reactions

693057

295817

295825

481084

14798

14797

Other Notes
手性阻旋异构双膦；铑和钌络合物可用于不对称氢化和异构化反应1,2,3；制备 BINAP-二羧酸钌络合物4

TRC

B386851

Chiral ligand for metal mediated asymmetric catalysis.

B386850

Chiral ligand for metal mediated asymmetric catalysis.

参考文献

PubChem文献

数据源提供

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2009)

• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)

• See also previous entry.

• The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).

• For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).

生物活性

PubChem BioAssay

化合物信息

ID:69483