编辑“︁BINAP”︁

{{chembox
| verifiedrevid = 406800255
| ImageFile =  BINAP axis.svg
| ImageSize = 
| ImageFile1 = 
| ImageSize1 = 
| IUPACName = (2R,3S)-2,2'-双二苯膦基-1,1'-联萘
| OtherNames = BINAP
| Section1 = {{Chembox Identifiers
|   CASNo = 76189-55-4
|   CASNo_Ref = {{cascite|correct|CAS}}
|   CASNo_Comment = ''R''
|   CASNo1 = 76189-56-5
|   CASNo1_Ref = {{cascite|correct|CAS}}
|   CASNo1_Comment = ''S''
|   PubChem = 634876
|   SMILES = 
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>44</sub>H<sub>32</sub>P<sub>2</sub>
|   MolarMass = 622.67
|   Appearance = 白色固体
|   Density =
|   MeltingPt = 239-241 °C (R), 238-240 °C (S)
|   BoilingPt = 
|   Solubility = 有机溶剂
  }}
| Section3 = {{Chembox Hazards
|   MainHazards = 
|   FlashPt = 
|   Autoignition = 
  }}
}}

[[Image:BINAP 3D.png|thumb|right|BINAP的球棍模型]]

'''BINAP''' 是有机化合物'''2,2'-双二苯膦基-1,1'-联萘'''的缩写。这种[[光学异构体|手性]][[配体]]广泛的应用于[[手性合成|不对称合成]]。它由一对2－二苯基膦[[萘|萘基]]连接1和1'位（图1）所组成。该C<sub>2</sub>-对称框架不存在[[手性中心|手性原子]]（参见[[轴向手性]]）。由于空间位阻，双萘环的消旋障碍很高从而限制了连接两萘环的化学键自由旋转（参见[[阻转异构体]]）。其萘环平面形成的[[二面角]]约为90˚。

== 应用 ==
在有机化学中，可使用BINAP与[[钌]]、[[铑]]和[[钯]]的[[络合物]]催化剂进行对映选择性反应。<ref>{{cite journal |last=Kitamura |first=Masato |coauthors=M. Tokunaga, T. Ohkuma, and R. Noyori |year=1998 |title=Asymmetric hydrogenation of 3-oxo carboxylates using BINAP-ruthenium complexes |journal=[[Org. Syn.]] |volume=9 |pages=589 |url=http://www.orgsynth.org/orgsyn/prep.asp?prep=cv9p0589 |access-date=2011-05-06 |archive-date=2011-07-18 |archive-url=https://web.archive.org/web/20110718024806/http://www.orgsynth.org/orgsyn/prep.asp?prep=cv9p0589 |dead-url=no }}</ref> 作为该领域的先驱， [[野依良治]]和他的同事发现，铑和BINAP的络合物对于合成(-)-[[薄荷醇]]非常有效。<ref>
{{cite journal |last=Akutagawa |first=S |year=1992 |title=A practical synthesis of (-)-menthol with the Rh-BINAP catalyst |journal= [[Chirality Ind.]] |pages=313−323}}</ref><ref>
{{cite journal |last=Kumobayashi |first=Hidenori |coauthors=Sayo, Noboru; Akutagawa, Susumu; Sakaguchi, Toshiaki; and Tsuruta, Haruki |year=1997 |title=Industrial asymmetric synthesis by use of metal-BINAP catalysts |journal= [[Nippon Kagaku Kaishi]] |volume=12 |pages=835−846}}</ref>

这种合成方法最早由[[高砂香料工業|高砂香料工業株式會社]]工业化。也因为这项工作，[[野依良治]]获得了2001年度的[[诺贝尔化学奖]]。

== 制备 ==
BINAP可通过BINOL（[[1,1'-联-2-萘酚]]）的二－三氟衍生物制备<ref>{{cite web |url=http://www.rhodia-phosphines.com/docs/Rhodia.pdf |title=BINAP: An industrial approach to manufacture |accessdate=2008-10-20 |publisher=[[Rhodia (company)]] |archive-date=2007-09-29 |archive-url=https://web.archive.org/web/20070929165900/http://www.rhodia-phosphines.com/docs/Rhodia.pdf |dead-url=no }}</ref><ref>{{cite journal |last=Cai |first=Dongwei |coauthors=J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, and P. J. Reider |year=2004 |title=(R)-(+)- and (S)-(−)-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP) |journal=[[Org. Syn.]] |volume=10 |pages=112 |url=http://www.orgsynth.org/orgsyn/prep.asp?prep=v76p0006 |access-date=2011-05-06 |archive-date=2011-07-18 |archive-url=https://web.archive.org/web/20110718024718/http://www.orgsynth.org/orgsyn/prep.asp?prep=v76p0006 |dead-url=no }}</ref> 
。R构型，S构型的[[对映体]]或其[[消旋体]]都是商业市售试剂。BINAP与铑共轭的试剂为一种广泛使用的化学选择性氢化催化剂。

BINOL可与{{link-en|氯代二苯基膦|Chlorodiphenylphosphine}}反应得到磷酸和二苯基-[1,1'-联萘]-2-2'-二醇酯（BINAPO）。<ref>{{cite journal |last=Nakajima |first=Makoto |coauthors=S. Kotani, T. Ishizuka, S. Hashimoto |year=2005 |title=Chiral Phosphine Oxide BINAPO as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilanes |journal= ChemInform |doi=10.1002/chin.200516031 |volume=36 }}</ref>

== 参考文献 ==
{{reflist}}

{{DEFAULTSORT:Binap}}

[[Category:二膦烷]]
[[Category:二苯基膦基化合物]]
[[Category:联萘]]