(R)-(+)-2-cyano-2'-diphenylphosphino-1,1'-binaphthyl | 156456-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(+)-2-cyano-2'-diphenylphosphino-1,1'-binaphthyl
• 英文别名: (R)-2-diphenylphosphino-2'-cyano-1,1'-binaphthalene；1-(2-Diphenylphosphanylnaphthalen-1-yl)naphthalene-2-carbonitrile
• CAS: 156456-69-8；176850-02-5
• 化学式: C₃₃H₂₂NP
• 分子量: 463.518
• InChiKey: TXXZXMMGZFQOLU-UHFFFAOYSA-N

物化性质

• 沸点：
  634.5±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-cyano-2'-diphenylphosphino-1,1'-binaphthyl 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-2-aminomethyl-2'-diphenylphosphino-1,1'-binaphthyl
  参考文献：
  名称：

  制备具有各种官能团的旋光联萘单膦（MOP）

  摘要：

  制备在C 2位具有氰基，氨基甲基，甲氧基羰基，羧基和羟甲基的各种官能团的旋光的2'-二苯基膦基-1,1'-联萘基（MOP's）。通过由光活性联萘酚容易制备的2-二苯基膦基-2'-三氟甲磺酰氧基1,1'-联萘的镍催化氰化作用，将氰基引入到MOP骨架上。带有羧基的MOP衍生物的制备是通过钯催化的2,2'-双萘基联萘的单羰基化，然后将剩余的三氟甲磺酸酯基进行膦化。

  DOI：

  10.1016/s0040-4020(01)89366-2
• 作为产物：
  描述：

  (R)-(+)-2-cyano-2'-diphenylphosphinyl-1,1'-binaphthyl 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到(R)-(+)-2-cyano-2'-diphenylphosphino-1,1'-binaphthyl
  参考文献：
  名称：

  制备具有各种官能团的旋光联萘单膦（MOP）

  摘要：

  制备在C 2位具有氰基，氨基甲基，甲氧基羰基，羧基和羟甲基的各种官能团的旋光的2'-二苯基膦基-1,1'-联萘基（MOP's）。通过由光活性联萘酚容易制备的2-二苯基膦基-2'-三氟甲磺酰氧基1,1'-联萘的镍催化氰化作用，将氰基引入到MOP骨架上。带有羧基的MOP衍生物的制备是通过钯催化的2,2'-双萘基联萘的单羰基化，然后将剩余的三氟甲磺酸酯基进行膦化。

  DOI：

  10.1016/s0040-4020(01)89366-2

文献信息

• Method for the Manufacture of Substituted Phosphanes, and Substituted Phosphanes Manufactured According to Said Method
  申请人：Thiel Werner

  公开号：US20080221335A1

  公开（公告）日：2008-09-11

  The invention relates to a method for the manufacture of substituted phosphanes and substituted phosphanes manufactured according to the method. Phosphanes, phosphane oxides, sulfides or selenides are used as ligands in coordination compounds. They play a central role in controlling the activity and selectivity of catalysts. The object is achieved by the invention by synthesizing heterocyclic substituents on aromatic groups by introducing acetyl groups. In this manner, previously unknown representatives of the families of phosphanes, phosphane oxides, sulfides and selenides are made accessible.

  本发明涉及一种制造取代膦和按照该方法制造的取代膦的方法。在配位化合物中，膦、膦氧化物、硫化物或硒化物被用作配体。它们在控制催化剂的活性和选择性方面起着核心作用。本发明通过在芳香族基团上引入乙酰基合成杂环取代基，从而实现了该目标。通过这种方法，膦、膦氧化物、硫化物和硒化物的新的未知代表得以获得。
• Optically active asymmetric diphosphine and process for producing
  申请人：Takasago International Corporation

  公开号：US05648548A1

  公开（公告）日：1997-07-15

  An optically active 2-diphenylphosphinomethyl-2'-diphenylphosphinyl-1,1'-binaphthalene derivative represented by the following general formula (I) ##STR1## wherein R represents a phenyl group, a tolyl group, an anisyl group or a chlorophenyl group, and a process for the production of optically active substances in which the above compound and a transition metal compound are used. The asymmetric diphosphine of the present invention is related to the creation of novel compounds, which is excellent as a ligand for asymmetric synthesis use. When the above compound is used together with a transition metal compound such as of ruthenium, rhodium or the like, it shows markedly excellent properties as the catalyst of asymmetric hydrogenation and the like reactions, in terms of selectivity, conversion ratio, catalytic activity and the like.

  以下是翻译结果： 一种光学活性的2-二苯基膦甲基-2'-二苯基膦基-1,1'-联萘衍生物，其通式如下（I）：##STR1## 其中R表示苯基、甲苯基、异丙基苯基或氯苯基，以及使用上述化合物和过渡金属化合物制备光学活性物质的方法。本发明的不对称二膦烷与新化合物的创造有关，作为不对称合成用配体而言，具有优异的性能。当上述化合物与铑、钌等过渡金属化合物一起使用时，在选择性、转化率、催化活性等方面，它表现出显著的优异性能，作为不对称氢化反应和其他反应的催化剂。
• Structural and ¹³C NMR Studies on Palladium MOP Compounds:  A New Weak C−Pd σ-Bond Plus MOP as a Bridging Diene Ligand
  作者：Pascal Dotta、P. G. Anil Kumar、Paul S. Pregosin、Alberto Albinati、Silvia Rizzato

  DOI：10.1021/om0496535

  日期：2004.8.1

  A new set of Pd-MOP complexes (MOP = (S)-2-diarylphosphino-1,1'-binaphthyl) has been prepared. One of these, containing MeO-MOP (=2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl), is shown to act as a chelating ligand with a naphthyl backbone diene bridging a Pd(I)-Pd(I) bond. This bonding mode exists in both the solid and solution states. A series of chloro-Pd(II)MOP complexes containing the well-known cyclometalated N V-dimethyl benzylamine chelate have been treated with NaBArF to extract the chloride ligand. The products, starting from the H-MOP, MeO-MOP, and NC-MOP analogues, are all different. Of particular interest is the product from the H-MOP reaction in that the fourth coordination position is occupied by a weak Pd-C sigma-bond from the naphthyl backbone, on the basis of C-13 NMR data. The rate of product formation in the Pd-catalyzed hydrosilylation of styrene with SiHCl3 has been measured as a function of time for the four auxiliaries H-MOP, MeO-MOP, HO-MOP, and NC-MOP. The NC-MOP is shown to be much faster than the others, and a tentative explanation is offered.
• Uozumi Yasuhiro, Suzuki Nobuhiro, Ogiwara Aya, Hayashi Tamio, Tetrahedron, 50 (1994) N 15, S 4293-4302
  作者：Uozumi Yasuhiro, Suzuki Nobuhiro, Ogiwara Aya, Hayashi Tamio

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG SUBSTITUIERTER PHOSPHANE
  申请人：Zylum Beteiligungsgesellschaft mbH & Co. Patente II KG

  公开号：EP1805193B1

  公开（公告）日：2010-12-29